format-version: 1.2 default-namespace: RXNO ontology: rxno.obo [Term] id: BFO:0000015 name: process [Term] id: BFO:0000016 name: disposition [Term] id: CHEBI:13759 name: alkylamine is_a: CHEBI:32877 ! primary amine [Term] id: CHEBI:15379 name: dioxygen is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:15734 name: primary alcohol is_a: CHEBI:30879 ! alcohol [Term] id: CHEBI:16227 name: pyridine is_a: CHEBI:26421 ! pyridines [Term] id: CHEBI:16240 name: hydrogen peroxide is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:16526 name: carbon dioxide is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:16670 name: peptide is_a: CHEBI:37622 ! carboxamide [Term] id: CHEBI:16842 name: formaldehyde is_a: CHEBI:17478 ! aldehyde [Term] id: CHEBI:17087 name: ketone is_a: CHEBI:36587 ! carbonyl compound [Term] id: CHEBI:17478 name: aldehyde is_a: CHEBI:36587 ! carbonyl compound [Term] id: CHEBI:17883 name: hydrogen chloride is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:18379 name: nitrile is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:22213 name: acridines is_a: CHEBI:35293 ! fused compound is_a: CHEBI:38101 ! azacycle [Term] id: CHEBI:22698 name: benzaldehydes is_a: CHEBI:17478 ! aldehyde [Term] id: CHEBI:22715 name: benzimidazoles is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:22929 name: bromoalkane is_a: CHEBI:24469 ! haloalkane [Term] id: CHEBI:23086 name: chalcones is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:23128 name: chloroalkane is_a: CHEBI:24469 ! haloalkane [Term] id: CHEBI:23252 name: cinnamic acids is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:23367 name: molecular entity is_a: CHEBI:24431 ! chemical entity disjoint_from: CHEBI:24433 ! group [Term] id: CHEBI:24043 name: flavones is_a: CHEBI:38104 ! oxacycle [Term] id: CHEBI:24129 name: furans is_a: CHEBI:38104 ! oxacycle [Term] id: CHEBI:24431 name: chemical entity [Term] id: CHEBI:24433 name: group is_a: CHEBI:24431 ! chemical entity [Term] id: CHEBI:24469 name: haloalkane is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:24828 name: indoles is_a: CHEBI:35293 ! fused compound is_a: CHEBI:38101 ! azacycle [Term] id: CHEBI:25000 name: lactone is_a: CHEBI:38104 ! oxacycle [Term] id: CHEBI:25717 name: organotin compound is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:25750 name: oxime is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:25996 name: phenylhydrazine is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:26410 name: pyrazoles is_a: CHEBI:38101 ! azacycle [Term] id: CHEBI:26421 name: pyridines is_a: CHEBI:38101 ! azacycle [Term] id: CHEBI:26455 name: pyrroles is_a: CHEBI:38101 ! azacycle [Term] id: CHEBI:26513 name: quinolines is_a: CHEBI:38101 ! azacycle [Term] id: CHEBI:26588 name: triazines is_a: CHEBI:38101 ! azacycle [Term] id: CHEBI:26708 name: sodium atom is_a: CHEBI:33521 [Term] id: CHEBI:26878 name: tertiary alcohol is_a: CHEBI:30879 ! alcohol [Term] id: CHEBI:26961 name: thiophenes is_a: CHEBI:38106 ! organosulfur heterocyclic compound [Term] id: CHEBI:27385 name: tetrachloromethane is_a: CHEBI:23128 ! chloroalkane [Term] id: CHEBI:27539 name: isatin is_a: CHEBI:24828 ! indoles [Term] id: CHEBI:278547 name: sodium azide is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:28112 name: nickel atom is_a: CHEBI:27081 [Term] id: CHEBI:28694 name: copper atom is_a: CHEBI:27081 [Term] id: CHEBI:28802 name: flavonols is_a: CHEBI:38104 ! oxacycle [Term] id: CHEBI:29224 name: dibromine is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:29785 name: nitro group is_a: CHEBI:24433 ! group [Term] id: CHEBI:30879 name: alcohol is_a: CHEBI:33822 ! organic hydroxy compound [Term] id: CHEBI:32816 name: pyruvic acid is_a: CHEBI:33575 ! carboxylic acid is_a: CHEBI:33860 ! aromatic amine [Term] id: CHEBI:32876 name: tertiary amine is_a: CHEBI:32952 ! amine [Term] id: CHEBI:32877 name: primary amine is_a: CHEBI:32952 ! amine [Term] id: CHEBI:32878 name: alkene is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:32952 name: amine is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:32955 name: epoxide is_a: CHEBI:38104 ! oxacycle [Term] id: CHEBI:32988 name: amide is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:33256 name: primary amide is_a: CHEBI:32988 ! amide [Term] id: CHEBI:33308 name: carboxylic ester is_a: CHEBI:36587 ! carbonyl compound [Term] id: CHEBI:33338 name: aryl group is_a: CHEBI:24433 ! group [Term] id: CHEBI:33341 name: titanium atom is_a: CHEBI:27081 [Term] id: CHEBI:33363 name: palladium atom is_a: CHEBI:27081 [Term] id: CHEBI:33364 name: platinum atom is_a: CHEBI:27081 [Term] id: CHEBI:33575 name: carboxylic acid is_a: CHEBI:36587 ! carbonyl compound [Term] id: CHEBI:33595 name: cyclic compound is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:33641 name: olefin is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:33822 name: organic hydroxy compound is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:33823 name: enol is_a: CHEBI:33822 ! organic hydroxy compound [Term] id: CHEBI:33839 name: macromolecule is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:33855 name: arenecarbaldehyde is_a: CHEBI:17478 ! aldehyde [Term] id: CHEBI:33860 name: aromatic amine is_a: CHEBI:32952 [Term] id: CHEBI:35293 name: fused compound is_a: CHEBI:33595 ! cyclic compound [Term] id: CHEBI:35403 name: chromium coordination entity is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:35636 name: carboximides is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:35681 name: secondary alcohol is_a: CHEBI:30879 ! alcohol [Term] id: CHEBI:35689 name: tetrazoles is_a: CHEBI:38101 ! azacycle [Term] id: CHEBI:35715 name: nitro compound is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:35886 name: tertiary phosphine is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:36587 name: carbonyl compound is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:36601 name: triphenylphosphane oxide is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:36605 name: phthalic anhydride is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:36606 name: acid anhydride is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:36687 name: acyl chloride is_a: CHEBI:37579 ! acyl halide [Term] id: CHEBI:36823 name: pseudohalo group is_a: CHEBI:24433 ! group [Term] id: CHEBI:37579 name: acyl halide is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:37602 name: allenes is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:37622 name: carboxamide is_a: CHEBI:33256 ! primary amide [Term] id: CHEBI:37757 name: iodoalkane is_a: CHEBI:24469 ! haloalkane [Term] id: CHEBI:38101 name: azacycle is_a: CHEBI:5686 ! heterocyclic compound [Term] id: CHEBI:38104 name: oxacycle is_a: CHEBI:5686 ! heterocyclic compound [Term] id: CHEBI:38106 name: organosulfur heterocyclic compound comment: I think this is the same as a thiacycle but need to check. synonym: "thiacycle" EXACT [] is_a: CHEBI:5686 ! heterocyclic compound [Term] id: CHEBI:38269 name: boronic acids is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:38757 name: isoflavones is_a: CHEBI:38104 ! oxacycle [Term] id: CHEBI:38784 name: oxetanes is_a: CHEBI:38104 ! oxacycle [Term] id: CHEBI:39141 name: Brønsted acid is_a: BFO:0000016 ! disposition [Term] id: CHEBI:39142 name: Brønsted base is_a: BFO:0000016 ! disposition [Term] id: CHEBI:39143 name: Lewis acid is_a: BFO:0000016 ! disposition [Term] id: CHEBI:39144 name: Lewis base is_a: BFO:0000016 ! disposition [Term] id: CHEBI:39447 name: pyrimidines is_a: CHEBI:38101 ! azacycle [Term] id: CHEBI:42485 name: formyl group is_a: CHEBI:24433 ! group [Term] id: CHEBI:43176 name: hydroxy group is_a: CHEBI:24433 ! group [Term] id: CHEBI:46882 name: amino group is_a: CHEBI:51142 ! amino groups [Term] id: CHEBI:46883 name: carboxy group is_a: CHEBI:24433 ! group [Term] id: CHEBI:47266 name: hydrogen bromide is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:47875 name: tetrabromomethane is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:48420 name: chromium trioxide is_a: CHEBI:35403 ! chromium coordination entity [Term] id: CHEBI:48513 name: carbazoles is_a: CHEBI:35293 ! fused compound is_a: CHEBI:38101 ! azacycle [Term] id: CHEBI:49553 name: copper(II) chloride is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:50075 name: dihydropyridine is_a: CHEBI:38101 ! azacycle [Term] id: CHEBI:50784 name: pivalate ester is_a: CHEBI:33308 ! carboxylic ester [Term] id: CHEBI:50888 name: fluoroarene is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:51080 name: nitrate ester is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:51142 name: amino groups is_a: CHEBI:24433 ! group [Term] id: CHEBI:51154 name: phosphonium ylide is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:51236 name: organomagnesium halide is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:51721 name: alpha,beta-unsaturated ketone is_a: CHEBI:17087 ! ketone [Term] id: CHEBI:51849 name: beta-ketoester is_a: CHEBI:17087 ! ketone is_a: CHEBI:33308 ! carboxylic ester [Term] id: CHEBI:51929 name: arylacetylene is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:52094 name: peroxy acid is_a: CHEBI:36587 ! carbonyl compound [Term] id: CHEBI:53434 name: palladium(II) chloride is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:55380 name: beta-hydroxy ketone is_a: CHEBI:17087 ! ketone [Term] id: CHEBI:5686 name: heterocyclic compound is_a: CHEBI:33595 ! cyclic compound [Term] id: CHEBI:59656 name: phosphine oxide is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:59831 name: enyne is_a: CHEBI:23367 ! molecular entity [Term] id: CHEBI:73477 name: terminal acetylenic compound is_a: CHEBI:73474 [Term] id: IAO:0000005 name: objective specification is_a: IAO:0000030 ! information content entity [Term] id: IAO:0000030 name: information content entity [Term] id: MOP:0000003 name: formylation def: "Formation of a covalent bond between a substrate and a formyl group." [RSC:xp] synonym: "formylation" EXACT [] is_a: MOP:0000479 ! acylation relationship: BFO:0000057 CHEBI:42485 ! has_participant formyl group [Term] id: MOP:0000339 name: silylation def: "Formation of a covalent bond between a substrate and an silyl group." [RSC:xp] comment: has_participant: CHEBI:33478 synonym: "silylation" EXACT [] is_a: MOP:0000566 ! formation of covalent bond with group [Term] id: MOP:0000364 name: methylation is_a: MOP:0000369 ! alkylation [Term] id: MOP:0000369 name: alkylation def: "Formation of a covalent bond between a substrate and an alkyl group." [RSC:xp] comment: has_participant: CHEBI:22323 synonym: "alkylation" EXACT [] is_a: MOP:0000410 ! hydrocarbylation [Term] id: MOP:0000410 name: hydrocarbylation def: "Formation of a covalent bond between a substrate and a hydrocarbyl group." [RSC:xp] comment: has_participant: CHEBI:33248 synonym: "hydrocarbylation" EXACT [] is_a: MOP:0000458 ! organylation [Term] id: MOP:0000411 name: arylation def: "Formation of a covalent bond between a substrate and an aryl group." [RSC:xp] synonym: "arylation" EXACT [] is_a: MOP:0000410 ! hydrocarbylation relationship: BFO:0000057 CHEBI:33338 ! has_participant aryl group [Term] id: MOP:0000422 name: allylation def: "Formation of a covalent bond between a substrate and an allyl group." [RSC:xp] comment: has_participant: CHEBI:30361 synonym: "allylation" EXACT [] is_a: MOP:0000410 ! hydrocarbylation [Term] id: MOP:0000458 name: organylation def: "Formation of a covalent bond between a substrate and an organyl group." [RSC:xp] comment: has_participant: CHEBI:33249 synonym: "organylation" EXACT [] is_a: MOP:0000566 ! formation of covalent bond with group [Term] id: MOP:0000479 name: acylation def: "Formation of a covalent bond between a substrate and an acyl group." [RSC:xp] comment: has_participant: CHEBI:22221 synonym: "acylation" EXACT [] is_a: MOP:0000458 ! organylation [Term] id: MOP:0000539 name: sulfonylation alt_id: MOP:0000524 def: "Formation of a covalent bond between a substrate and a sulfonyl group." [RSC:xp] comment: has_participant: CHEBI:51100; has_participant: CHEBI:29825 synonym: "sulfonylation" EXACT [] is_a: MOP:0000566 ! formation of covalent bond with group [Term] id: MOP:0000543 name: molecular process def: "A process in which at least one of the participants is a molecule." [http://orcid.org/0000-0001-5985-7429] comment: TODO: needs work, formal definition, etc. is_a: BFO:0000015 ! process [Term] id: MOP:0000550 name: halogenation def: "Formation of a covalent bond between a substrate and a halo group." [RSC:xp] comment: has_participant: CHEBI:47854 is_a: MOP:0000566 ! formation of covalent bond with group [Term] id: MOP:0000555 name: imination def: "Formation of a covalent bond between a substrate and an imino group." [RSC:xp] comment: has_participant: CHEBI:29342 is_a: MOP:0000802 ! formation of covalent bond with nitrogen centre [Term] id: MOP:0000556 name: nitration def: "Formation of a covalent bond between a substrate and a nitro group." [RSC:xp] is_a: MOP:0000566 ! formation of covalent bond with group relationship: BFO:0000057 CHEBI:29785 ! has_participant nitro group [Term] id: MOP:0000561 name: cyclization def: "Formation of a ring in a molecule from a chain by formation of a new bond." [AU:C01494] synonym: "cyclisation" EXACT [] is_a: MOP:0000543 ! molecular process relationship: BFO:0000077 CHEBI:33595 ! has participant beginning to exist cyclic compound [Term] id: MOP:0000562 name: cycloaddition alt_id: RXNO:0000314 def: "A molecular process where two or more unsaturated molecules or parts of the same molecule combine to form a cyclic adduct in which there is a net reduction of bond multiplicity." [AU:C01496] is_a: MOP:0000561 ! cyclization [Term] id: MOP:0000563 name: [2+2] cycloaddition def: "A cycloaddition in which each participant contributes two electrons to the transformation of reactants to products." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000562 ! cycloaddition [Term] id: MOP:0000564 name: cycloelimination def: "A molecular process in which a cyclic system decomposes into two or more unsaturated molecules or parts of the same molecule and there is a net increase in bond multiplicity." [AU:C01496, AU:C01501] synonym: "cycloreversion" EXACT [AU:C01506] synonym: "retro-addition" EXACT [] synonym: "retrocycloaddition" EXACT [AU:R05372] is_a: MOP:0000543 ! molecular process [Term] id: MOP:0000565 name: [4+2] cycloaddition def: "A cycloaddition in which one participant contributes four electrons and the other participant contributes two electrons to the transformation of reactants to products." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000562 ! cycloaddition relationship: BFO:0000055 MOP:0000826 [Term] id: MOP:0000566 name: formation of covalent bond with group def: "Formation of a covalent bond between a substrate and a group." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000543 ! molecular process created_by: batchelorc creation_date: 2009-04-22T10:01:32Z [Term] id: MOP:0000567 name: breaking of covalent bond with group def: "Breaking of a covalent bond between a substrate and a group." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000543 ! molecular process created_by: batchelorc creation_date: 2009-04-30T02:24:32Z [Term] id: MOP:0000568 name: oxidation def: "The complete, net removal of one or mole electrons from a molecular entity, corresponding to an increase in the oxidation number of any atom within any substrate." [AU:O04362] synonym: "de-electronation" EXACT [] is_a: MOP:0000543 ! molecular process created_by: batchelorc creation_date: 2009-06-01T06:01:47Z [Term] id: MOP:0000569 name: reduction def: "The complete transfer of one or more electrons to a molecular entity." [AU:R05222] synonym: "electronation" EXACT [] is_a: MOP:0000543 ! molecular process created_by: batchelorc creation_date: 2009-06-01T06:04:18Z [Term] id: MOP:0000570 name: electron attachment def: "The transfer of an electron to a molecular entity, resulting in a molecular entity of increased negative charge." [AU:E01979] is_a: MOP:0000569 ! reduction created_by: batchelorc creation_date: 2009-06-01T06:06:19Z [Term] id: MOP:0000571 name: aldehyde reduction def: "A reduction in which an aldehyde is reduced to form a primary alcohol." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000569 ! reduction relationship: BFO:0000077 CHEBI:15734 ! has participant beginning to exist primary alcohol relationship: BFO:0000078 CHEBI:17478 ! has participant ceasing to exist aldehyde created_by: batchelorc creation_date: 2009-06-01T06:07:02Z [Term] id: MOP:0000572 name: alcohol oxidation def: "An oxidation process where an alcohol is transformed into a carbonyl compound." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000568 ! oxidation relationship: BFO:0000078 CHEBI:30879 ! has participant ceasing to exist alcohol created_by: batchelorc creation_date: 2009-06-01T06:10:35Z [Term] id: MOP:0000573 name: primary alcohol oxidation to aldehyde def: "An oxidation process where a primary alcohol is transformed into an aldehyde." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000572 ! alcohol oxidation relationship: BFO:0000077 CHEBI:17478 ! has participant beginning to exist aldehyde relationship: BFO:0000078 CHEBI:15734 ! has participant ceasing to exist primary alcohol created_by: batchelorc creation_date: 2009-06-01T06:10:59Z [Term] id: MOP:0000574 name: secondary alcohol oxidation to ketone def: "An oxidation process where a secondary alcohol is transformed into a ketone." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000572 ! alcohol oxidation relationship: BFO:0000077 CHEBI:17087 ! has participant beginning to exist ketone relationship: BFO:0000078 CHEBI:35681 ! has participant ceasing to exist secondary alcohol created_by: batchelorc creation_date: 2009-06-01T06:11:31Z [Term] id: MOP:0000575 name: amine oxidation def: "An oxidation process where an amine is transformed into an imine." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000706 ! oxidation at nitrogen created_by: batchelorc creation_date: 2009-06-01T06:15:40Z [Term] id: MOP:0000576 name: imine reduction def: "A reduction process where an imine is transformed into an amine." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000569 ! reduction created_by: batchelorc creation_date: 2009-06-01T06:19:21Z [Term] id: MOP:0000577 name: ester reduction def: "A reduction process where the oxidation state carbonyl carbon in the ester functionality is reduced." [http://orcid.org/0000-0001-5985-7429] synonym: "reduction of ester" EXACT [] is_a: MOP:0000569 ! reduction relationship: BFO:0000078 CHEBI:33308 ! has participant ceasing to exist carboxylic ester created_by: batchelorc creation_date: 2009-06-02T05:30:48Z [Term] id: MOP:0000578 name: ester reduction to aldehyde def: "An ester reduction where the product is the corresponding aldehyde." [http://orcid.org/0000-0001-5985-7429] synonym: "reduction of ester to aldehyde" EXACT [] synonym: "reduction of esters to aldehyde" EXACT [] is_a: MOP:0000577 ! ester reduction relationship: BFO:0000077 CHEBI:17478 ! has participant beginning to exist aldehyde created_by: batchelorc creation_date: 2009-06-02T05:31:49Z [Term] id: MOP:0000579 name: ester reduction to primary alcohol def: "An ester reduction where the product is the corresponding primary alcohol." [http://orcid.org/0000-0001-5985-7429] synonym: "reduction of ester to primary alcohol" EXACT [] synonym: "reduction of esters to primary alcohol" EXACT [] is_a: MOP:0000577 ! ester reduction relationship: BFO:0000077 CHEBI:15734 ! has participant beginning to exist primary alcohol created_by: batchelorc creation_date: 2009-06-02T05:32:37Z [Term] id: MOP:0000580 name: ketone reduction def: "A reduction process where a ketone is reduced to a secondary alcohol." [http://orcid.org/0000-0001-5985-7429] synonym: "reduction of ketone" EXACT [] synonym: "reduction of ketones" EXACT [] is_a: MOP:0000569 ! reduction relationship: BFO:0000077 CHEBI:35681 ! has participant beginning to exist secondary alcohol relationship: BFO:0000078 CHEBI:17087 ! has participant ceasing to exist ketone created_by: batchelorc creation_date: 2009-06-02T05:35:42Z [Term] id: MOP:0000581 name: alkene oxidation def: "An oxidation process where the oxidation state of at least one doubly-bonded carbon atom increases." [http://orcid.org/0000-0001-5985-7429] synonym: "olefin oxidation" EXACT [] is_a: MOP:0000568 ! oxidation created_by: batchelorc creation_date: 2009-06-02T05:45:30Z [Term] id: MOP:0000582 name: alkene oxidation to 1,2-diol def: "An alkene oxidation where the product is the corresponding 1,2-diol." [http://orcid.org/0000-0001-5985-7429] synonym: "alkene oxidation to glycol" EXACT [] synonym: "oxidation of alkene to 1,2-diol" EXACT [] synonym: "oxidation of alkenes to 1,2-diol" EXACT [] is_a: MOP:0000581 ! alkene oxidation created_by: batchelorc creation_date: 2009-06-02T05:46:52Z [Term] id: MOP:0000583 name: alkene ozonolysis def: "An alkene oxidation where the reagent is ozone and the product is the corresponding ozonide." [http://orcid.org/0000-0001-5985-7429] synonym: "ozonolysis of alkene" EXACT [] synonym: "ozonolysis of alkenes" EXACT [] is_a: RXNO:0000344 ! alkene oxidative cleavage created_by: batchelorc creation_date: 2009-06-02T05:48:42Z [Term] id: MOP:0000584 name: primary alkene oxidation to carboxylic acid and carbon dioxide def: "An alkene oxidation process where the reactant is a primary alkene and the products are carboxylic acid and carbon dioxide. This can be achieved with a warm, acidic solution of potassium permanganate." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000344 ! alkene oxidative cleavage relationship: BFO:0000077 CHEBI:16526 ! has participant beginning to exist carbon dioxide created_by: batchelorc creation_date: 2009-06-02T06:02:46Z [Term] id: MOP:0000585 name: tertiary alkene oxidation to carboxylic acid and ketone def: "An alkene oxidation where the reactant is a tertiary alkene and the products are the corresponding carboxylic acid and ketone. This can be achieved with a warm, acidic solution of potassium permanganate." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000344 ! alkene oxidative cleavage relationship: BFO:0000077 CHEBI:17087 ! has participant beginning to exist ketone created_by: batchelorc creation_date: 2009-06-02T06:04:14Z [Term] id: MOP:0000586 name: secondary, non-terminal alkene oxidation to aldehydes def: "An alkene oxidation process where the reactant is a secondary alkene and the products are the corresponding aldehydes. This can be achieved with warm, acidic potassium permanganate." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000344 ! alkene oxidative cleavage relationship: BFO:0000077 CHEBI:17478 ! has participant beginning to exist aldehyde created_by: batchelorc creation_date: 2009-06-02T06:06:23Z [Term] id: MOP:0000587 name: secondary terminal alkene oxidation to ketone and carbon dioxide def: "An alkene oxidation process where the reactant is a secondary terminal alkene and the products are carbon dioxide and the corresponding ketone. This can be achieved by warm, acidic potassium permanganate solution." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000344 ! alkene oxidative cleavage relationship: BFO:0000077 CHEBI:16526 ! has participant beginning to exist carbon dioxide relationship: BFO:0000077 CHEBI:17087 ! has participant beginning to exist ketone created_by: batchelorc creation_date: 2009-06-02T06:07:44Z [Term] id: MOP:0000588 name: quaternary alkene oxidation to ketones def: "An alkene oxidation process where the reactant is a quaternary alkene and the products are the corresponding ketones." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000344 ! alkene oxidative cleavage relationship: BFO:0000077 CHEBI:17087 ! has participant beginning to exist ketone created_by: batchelorc creation_date: 2009-06-02T06:09:24Z [Term] id: MOP:0000589 name: hydrogenation def: "A reduction process that involves addition of hydrogen atoms across a double bond." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000569 ! reduction created_by: batchelorc creation_date: 2009-06-05T04:53:34Z [Term] id: MOP:0000596 name: pseudohalogenation def: "Formation of a covalent bond between a substrate and a pseudohalo group." [RSC:xp] is_a: MOP:0000566 ! formation of covalent bond with group relationship: BFO:0000057 CHEBI:36823 ! has_participant pseudohalo group [Term] id: MOP:0000627 name: condensation reaction alt_id: RXNO:0000315 def: "A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of a small molecule." [AU:C01238] is_a: MOP:0000543 ! molecular process created_by: batchelorc creation_date: 2009-09-16T11:30:32Z [Term] id: MOP:0000628 name: molecular dehydration reaction def: "A condensation reaction where the small molecule produced is water." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000627 ! condensation reaction created_by: batchelorc creation_date: 2009-09-16T11:32:33Z [Term] id: MOP:0000650 name: amination def: "Formation of a covalent bond between a substrate and an amino group." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000802 ! formation of covalent bond with nitrogen centre relationship: BFO:0000057 CHEBI:51142 ! has_participant amino groups [Term] id: MOP:0000656 name: elimination reaction def: "A molecular process where two groups are lost with concomitant formation of an unsaturation in the molecule or formation of a new ring." [doi:10.1351/goldbook.E02038] is_a: MOP:0000543 ! molecular process [Term] id: MOP:0000671 name: epoxidation def: "A cyclisation that results in the formation of an epoxide." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000561 ! cyclization relationship: BFO:0000077 CHEBI:32955 ! has participant beginning to exist epoxide [Term] id: MOP:0000705 name: oxidation at sulfur def: "An oxidation process where the oxidation state of at least one sulfur atom increases." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000568 ! oxidation [Term] id: MOP:0000706 name: oxidation at nitrogen def: "An oxidation process where the oxidation state of at least one nitrogen atom increases." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000568 ! oxidation [Term] id: MOP:0000712 name: oxidation state def: "A formal account of the degree of oxidation of an atom." [http://orcid.org/0000-0001-5985-7429] comment: It turns out to be formally defined, which makes our definitions a bit poor. xref: http://goldbook.iupac.org/O04365.html is_a: IAO:0000030 ! information content entity [Term] id: MOP:0000713 name: carboxylation def: "Formation of a covalent bond between a molecule and a carboxy group." [RSC:xp] is_a: MOP:0000479 ! acylation relationship: BFO:0000057 CHEBI:46883 ! has_participant carboxy group [Term] id: MOP:0000714 name: carbonyl oxidation to alkyne def: "Oxidation of a carbonyl group to an alkyne." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000568 ! oxidation [Term] id: MOP:0000715 name: [3+2] cycloaddition def: "A cycloaddition in which one participant contributes three electrons and the other participant contributes two electrons to the transformation of reactants to products." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000562 ! cycloaddition [Term] id: MOP:0000716 name: enolisation def: "Molecular process in which an aldehyde or ketone tautomerises to form an enol." [http://orcid.org/0000-0001-5985-7429] synonym: "enolization" EXACT [] is_a: MOP:0000543 ! molecular process intersection_of: MOP:0000543 ! molecular process intersection_of: BFO:0000055 MOP:0000717 ! realizes enolisability relationship: BFO:0000055 MOP:0000717 ! realizes enolisability relationship: BFO:0000077 CHEBI:33823 ! has participant beginning to exist enol [Term] id: MOP:0000717 name: enolisability def: "Disposition that is realised in the process of enolisation" [http://orcid.org/0000-0001-5985-7429] is_a: BFO:0000016 ! disposition [Term] id: MOP:0000718 name: enolisable carbonyl compound def: "A carbonyl compound that bears the disposition to be enolised." [http://orcid.org/0000-0001-5985-7429] comment: this surely belongs in ChEBI but put it here pro tem is_a: CHEBI:36587 ! carbonyl compound intersection_of: CHEBI:36587 ! carbonyl compound intersection_of: BFO:0000162 MOP:0000717 ! has disposition at all times enolisability relationship: BFO:0000162 MOP:0000717 ! has disposition at all times enolisability [Term] id: MOP:0000719 name: O-dealkylation def: "Breaking of a covalent bond between an alkyl group and an oxygen atom." [RSC:xp] is_a: MOP:0001369 ! dealkylation [Term] id: MOP:0000720 name: [2+2+1] cycloaddition def: "A cycloaddition in which two participants contribute two electrons and the other participant contributes one electron to the transformation of reactants to products." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000562 ! cycloaddition [Term] id: MOP:0000721 name: [3,3]-sigmatropic rearrangement alt_id: RXNO:0000027 comment: This term was obsoleted from the RXNO namespace and transferred to MOP because it is a process identifiable by its mechanism rather than the intention of the experimenter. is_a: MOP:0000543 ! molecular process [Term] id: MOP:0000722 name: decarboxylative condensation def: "A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of a carbon dioxide molecule." [RSC:xp] is_a: MOP:0000627 ! condensation reaction relationship: has_part MOP:0001713 ! decarboxylation created_by: batchelorc creation_date: 2014-03-05T10:00:00Z [Term] id: MOP:0000723 name: deethanolative condensation def: "A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of an ethanol molecule." [RSC:xp] is_a: MOP:0000825 ! dealcholative condensation reaction created_by: batchelorc creation_date: 2014-03-05T10:00:00Z [Term] id: MOP:0000730 name: Brønsted acid catalysis is_a: MOP:0000740 ! acid catalysis created_by: batchelorc creation_date: 2014-04-09T10:00:00Z [Term] id: MOP:0000731 name: base catalysis is_a: MOP:0000543 ! molecular process union_of: MOP:0000735 ! Lewis base catalysis union_of: MOP:0000736 ! Brønsted base catalysis created_by: batchelorc creation_date: 2014-04-09T10:00:00Z [Term] id: MOP:0000732 name: hydron donation is_a: MOP:0000543 ! molecular process relationship: BFO:0000055 CHEBI:39141 ! realizes Brønsted acid created_by: batchelorc creation_date: 2014-04-09T10:00:00Z [Term] id: MOP:0000733 name: accepting an electron pair in Lewis adduct formation is_a: MOP:0000543 ! molecular process relationship: BFO:0000055 CHEBI:39143 ! realizes Lewis acid created_by: batchelorc creation_date: 2014-04-09T10:00:00Z [Term] id: MOP:0000734 name: Lewis acid catalysis is_a: MOP:0000740 ! acid catalysis created_by: batchelorc creation_date: 2014-04-09T10:00:00Z [Term] id: MOP:0000735 name: Lewis base catalysis is_a: MOP:0000731 ! base catalysis created_by: batchelorc creation_date: 2014-04-09T10:00:00Z [Term] id: MOP:0000736 name: Brønsted base catalysis is_a: MOP:0000731 ! base catalysis relationship: has_part MOP:0000737 ! accepting a hydron created_by: batchelorc creation_date: 2014-04-09T10:00:00Z [Term] id: MOP:0000737 name: accepting a hydron is_a: MOP:0000543 ! molecular process relationship: BFO:0000055 CHEBI:39142 ! realizes Brønsted base created_by: batchelorc creation_date: 2014-04-09T10:00:00Z [Term] id: MOP:0000738 name: electron pair donation in Lewis adduct formation is_a: MOP:0000543 ! molecular process relationship: BFO:0000055 CHEBI:39144 ! realizes Lewis base created_by: batchelorc creation_date: 2014-04-09T10:00:00Z [Term] id: MOP:0000739 name: Lewis adduct formation is_a: MOP:0000543 ! molecular process relationship: has_part MOP:0000733 ! accepting an electron pair in Lewis adduct formation relationship: has_part MOP:0000738 ! electron pair donation in Lewis adduct formation [Term] id: MOP:0000740 name: acid catalysis def: "Catalysis of a reaction where the catalyst either donates a hydron or accepts an electron pair." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000543 ! molecular process union_of: MOP:0000730 ! Brønsted acid catalysis union_of: MOP:0000734 ! Lewis acid catalysis [Term] id: MOP:0000790 name: substitution reaction alt_id: RXNO:0000019 def: "A reaction in which one singly-bonded group, but not the hydrogen atom, is replaced by another singly-bonded group." [http://orcid.org/0000-0001-5985-7429] comment: The Gold Book says hydrogen atoms count, but this differs from everyone's intuition. See http://goldbook.iupac.org/S06078.html is_a: MOP:0000543 ! molecular process [Term] id: MOP:0000791 name: aromatic substitution alt_id: RXNO:0000020 def: "A substitution reaction in which one singly-bonded substituent on an aromatic skeleton is replaced by another singly-bonded substituent." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000790 ! substitution reaction [Term] id: MOP:0000792 name: allylic rearrangement alt_id: RXNO:0000033 def: "A substitution reaction in an allylic system with concomitant migration of the allyl double bond." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: MOP:0000790 ! substitution reaction [Term] id: MOP:0000793 name: N-substitution alt_id: RXNO:0000319 def: "A substitution reaction where the reactive centre is a nitrogen atom." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000790 ! substitution reaction [Term] id: MOP:0000794 name: O-substitution alt_id: RXNO:0000318 def: "A substitution reaction where the reactive centre is an oxygen atom." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:1.7 is_a: MOP:0000790 ! substitution reaction [Term] id: MOP:0000795 name: S-substitution alt_id: RXNO:0000336 def: "A substitution reaction where the reactive centre is a sulfur atom." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:1.8 is_a: MOP:0000790 ! substitution reaction created_by: batchelorc creation_date: 2012-03-22T12:22:59Z [Term] id: MOP:0000802 name: formation of covalent bond with nitrogen centre def: "Formation of a covalent bond with a group where the free valence is on a nitrogen centre." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000566 ! formation of covalent bond with group [Term] id: MOP:0001369 name: dealkylation def: "Breaking of a covalent bond between an alkyl group and a substrate." [RSC:xp] is_a: MOP:0001458 ! deorganylation [Term] id: MOP:0001458 name: deorganylation def: "Breaking of a covalent bond between a substrate and an organyl group." [RSC:xp] comment: has_participant: CHEBI:33249 is_a: MOP:0000567 ! breaking of covalent bond with group [Term] id: MOP:0001550 name: dehalogenation def: "Breaking of a covalent bond between a substrate and a halo group." [RSC:xp] comment: has_participant: CHEBI:47854 is_a: MOP:0000567 ! breaking of covalent bond with group [Term] id: MOP:0001713 name: decarboxylation def: "Breaking of a covalent bond between a molecule and a carboxy group." [RSC:xp] is_a: MOP:0001458 ! deorganylation relationship: BFO:0000057 CHEBI:46883 ! has_participant carboxy group relationship: BFO:0000077 CHEBI:16526 ! has participant beginning to exist carbon dioxide [Term] id: MOP:0002364 name: N-methylation def: "Formation of a covalent bond between a nitrogen atom in a substrate and a methyl group." [RSC:xp] comment: has_participant: CHEBI:32875 is_a: MOP:0000364 ! methylation [Term] id: MOP:0002369 name: N-alkylation def: "Formation of a covalent bond between a nitrogen atom in a substrate and an alkyl group." [RSC:xp] comment: has_participant: CHEBI:22323 is_a: MOP:0000369 ! alkylation [Term] id: MOP:0002411 name: N-arylation def: "Formation of a covalent bond between a nitrogen atom in a substrate and an aryl group." [RSC:xp] is_a: MOP:0000411 ! arylation relationship: BFO:0000057 CHEBI:33338 ! has_participant aryl group [Term] id: MOP:0002479 name: N-acylation def: "Formation of a covalent bond between a nitrogen atom in a substrate and an acyl group." [RSC:xp] comment: has_participant: CHEBI:22221 is_a: MOP:0000479 ! acylation [Term] id: MOP:0002524 name: N-sulfonylation def: "Formation of a covalent bond between a nitrogen atom in a substrate and a sulfonyl group." [RSC:xp] comment: has_participant: CHEBI:29825 is_a: MOP:0000539 ! sulfonylation [Term] id: MOP:0003339 name: O-silylation def: "Formation of a covalent bond between an oxygen atom in a substrate and a silyl group." [RSC:xp] comment: has_participant: CHEBI:30541 is_a: MOP:0000339 ! silylation [Term] id: MOP:0003479 name: O-acylation def: "Formation of a covalent bond between an oxygen atom in a substrate and an acyl group." [RSC:xp] comment: has_participant: CHEBI:22221 is_a: MOP:0000479 ! acylation [Term] id: MOP:0003524 name: O-sulfonylation def: "Formation of a covalent bond between an oxygen atom in a substrate and a sulfonyl group." [RSC:xp] comment: has_participant: CHEBI:29825 is_a: MOP:0000539 ! sulfonylation [Term] id: MOP:0006369 name: P-alkylation def: "The formation of a covalent bond between a phosphorus atom and an alkyl group." [RSC:xp] is_a: MOP:0000369 ! alkylation [Term] id: OBI:0000011 name: planned process is_a: BFO:0000015 [Term] id: RXNO:0000000 name: molecular skeleton joining reaction def: "A reaction where the number of atoms in the molecular skeleton increases." [http://orcid.org/0000-0001-5985-7429] synonym: "coupling reaction" EXACT [] is_a: RXNO:0000001 ! planned reaction step is_a: RXNO:0000002 ! carbon-carbon coupling reaction intersection_of: RXNO:0000002 ! carbon-carbon coupling reaction intersection_of: OBI:0000417 RXNO:0000440 ! achieves_planned_objective molecular skeleton joining objective relationship: OBI:0000417 RXNO:0000440 ! achieves_planned_objective molecular skeleton joining objective [Term] id: RXNO:0000001 name: planned reaction step def: "A molecular process with which the experimenters aim to achieve a particular molecular transformation." [http://orcid.org/0000-0001-5985-7429] is_a: OBI:0000011 ! planned process intersection_of: OBI:0000011 ! planned process intersection_of: OBI:0000417 RXNO:0000437 ! achieves_planned_objective molecular transformation objective relationship: OBI:0000417 RXNO:0000437 ! achieves_planned_objective molecular transformation objective relationship: part_of RXNO:0000329 ! planned synthesis [Term] id: RXNO:0000002 name: carbon-carbon coupling reaction def: "A reaction where a bond is formed between two carbon atoms." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:3 is_a: MOP:0000543 ! molecular process [Term] id: RXNO:0000003 name: Perkin reaction def: "An aldol condensation where an aryl aldehyde reacts with an acid anhydride to form a cinnamic acid." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000327/ is_a: RXNO:0000017 ! aldol condensation relationship: RXNO:0000423 CHEBI:23252 ! has specified product cinnamic acids relationship: RXNO:0000424 CHEBI:33855 ! has specified reactant arenecarbaldehyde relationship: RXNO:0000424 CHEBI:36606 ! has specified reactant acid anhydride [Term] id: RXNO:0000004 name: ring reaction def: "A reaction in which the number of atoms in any ring changes between the reactant and the products." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] comment: This term was obsoleted because it was a grouping term that wasn't much help. is_obsolete: true [Term] id: RXNO:0000005 name: ring formation reaction step def: "A planned reaction step where the product contains a ring that was not in any of the reactants." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000561 ! cyclization is_a: RXNO:0000001 ! planned reaction step intersection_of: MOP:0000543 ! molecular process intersection_of: RXNO:0000423 CHEBI:33595 ! has specified product cyclic compound relationship: OBI:0000417 RXNO:0000439 ! achieves_planned_objective molecular ring formation objective relationship: RXNO:0000423 CHEBI:33595 ! has specified product cyclic compound [Term] id: RXNO:0000006 name: Diels-Alder reaction def: "A [4+2] cycloaddition reaction where a diene reacts with a compound containing a double or triple bond (a dienophile) to form an unsaturated six-membered ring compound." [http://orcid.org/0000-0002-4077-4719] synonym: "Diels-Alder coupling" EXACT [] synonym: "Diels-Alder cycloaddition" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000109/ xref: https://en.wikipedia.org/wiki/Diels-Alder_reaction xref: NAMERXN:3.11.3 is_a: MOP:0000565 ! [4+2] cycloaddition [Term] id: RXNO:0000007 name: ene reaction def: "A joining reaction where an alkene with an allylic hydrogen reacts with a compound containing a multiple bond (an enophile) to form a substituted alkene." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000129/ is_a: RXNO:0000000 ! molecular skeleton joining reaction [Term] id: RXNO:0000008 name: conjugate addition def: "A joining reaction where a nucleophile adds to the beta-carbon of an alpha,beta-unsaturated system (or an activated carbon-carbon bond)." [http://orcid.org/0000-0002-4077-4719, rsc:db] synonym: "nucleophilic conjugate addition" EXACT [] xref: http://en.wikipedia.org/wiki/Nucleophilic_conjugate_addition is_a: RXNO:0000000 ! molecular skeleton joining reaction [Term] id: RXNO:0000009 name: Michael addition def: "A conjugate addition reaction where a carbon nucleophile adds to the beta-carbon of an alpha,beta-unsaturated system (or an activated carbon-carbon bond)." [RSC:db] synonym: "Michael reaction" EXACT [] xref: http://en.wikipedia.org/wiki/Michael_reaction xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000281/ is_a: RXNO:0000008 ! conjugate addition [Term] id: RXNO:0000010 name: functional modification def: "A reaction where the number of atoms in the skeleton, and their connectivity, remain the same." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000001 ! planned reaction step intersection_of: RXNO:0000001 ! planned reaction step intersection_of: OBI:0000417 RXNO:0000442 ! achieves_planned_objective functional modification objective relationship: OBI:0000417 RXNO:0000442 ! achieves_planned_objective functional modification objective [Term] id: RXNO:0000011 name: functional group modification def: "A reaction in which a functional group undergoes a change that does not affect the number of atoms in (or connectivity of) the skeleton of the molecule." [rsc:db] xref: NAMERXN:9 is_a: RXNO:0000010 ! functional modification intersection_of: RXNO:0000010 ! functional modification intersection_of: OBI:0000417 RXNO:0000453 ! achieves_planned_objective functional group modification objective relationship: OBI:0000417 RXNO:0000453 ! achieves_planned_objective functional group modification objective [Term] id: RXNO:0000012 name: functional group oxidation def: "A functional group modification reaction where a functional group is oxidised." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000568 ! oxidation is_a: RXNO:0000011 ! functional group modification intersection_of: RXNO:0000011 ! functional group modification intersection_of: OBI:0000417 RXNO:0000490 ! achieves_planned_objective functional oxidation objective relationship: OBI:0000417 RXNO:0000490 ! achieves_planned_objective functional oxidation objective [Term] id: RXNO:0000013 name: diazotisation def: "A functional group oxidation where an aromatic amine is transformed into an aromatic diazonium salt." [http://orcid.org/0000-0002-4077-4719] synonym: "diazotization" EXACT [] is_a: RXNO:0000012 ! functional group oxidation relationship: RXNO:0000424 CHEBI:33860 ! has specified reactant aromatic amine [Term] id: RXNO:0000014 name: Grignard reaction def: "A carbon-carbon coupling reaction where a Grignard reagent reacts with a compound containing an electrophilic carbon atom. A Grignard reagent is a magnesium-stabilised carbon nucleophile. An aldehyde leads to a secondary alcohol, a ketone leads to a tertiary alcohol, an ester leads to a ketone and a nitrile leads to a ketone." [RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000177/ xref: NAMERXN:3.7 is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: RXNO:0000424 CHEBI:51236 ! has specified reactant organomagnesium halide [Term] id: RXNO:0000015 name: Wittig reaction def: "A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give an alkene." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Wittig condensation" EXACT [] synonym: "Wittig olefination" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/r468/ xref: NAMERXN:3.8 is_a: RXNO:0000479 ! olefination relationship: RXNO:0000423 CHEBI:33641 ! has specified product olefin relationship: RXNO:0000424 CHEBI:51154 ! has specified reactant phosphonium ylide [Term] id: RXNO:0000016 name: aldol addition def: "A carbon-carbon coupling reaction where an enol or enolate reacts with a carbonyl compound to form a beta-hydroxy ketone. The name comes from aldehyde + alcohol." [http://orcid.org/0000-0001-5985-7429] synonym: "aldol reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000004/ is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: RXNO:0000423 CHEBI:55380 ! has specified product beta-hydroxy ketone [Term] id: RXNO:0000017 name: aldol condensation def: "An aldol addition where an enol or enolate reacts with a carbonyl compound to form an alpha,beta-unsaturated ketone." [http://orcid.org/0000-0002-4077-4719] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000004/ is_a: MOP:0000628 ! molecular dehydration reaction is_a: RXNO:0000016 ! aldol addition relationship: RXNO:0000423 CHEBI:51721 ! has specified product alpha,beta-unsaturated ketone [Term] id: RXNO:0000018 name: 1,3-dipolar cycloaddition def: "A ring formation reaction where a 1,3-dipolar compound reacts with an alkene or alkyne to form a five-membered ring compound." [RSC:db] synonym: "Huisgen cycloaddition" NARROW [] synonym: "Huisgen reaction" NARROW [] synonym: "Huisgen's 1,3-dipolar cycloaddition" NARROW [] is_a: MOP:0000562 ! cycloaddition [Term] id: RXNO:0000021 name: Sandmeyer reaction def: "An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) halide or pseudohalide to form an aromatic halide or pseudohalide." [RSC:db] xref: http://en.wikipedia.org/wiki/Sandmeyer_reaction xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000386/ is_a: RXNO:0000332 ! aromatic substitution step union_of: RXNO:0000333 ! Sandmeyer halogenation union_of: RXNO:0000334 ! Sandmeyer pseudohalogenation [Term] id: RXNO:0000022 name: Gattermann halogenation def: "An aromatic substitution reaction where an aryl diazonium salt reacts with copper powder and hydrochloric acid or hydrobromic acid to form an aromatic chloride or bromide." [http://orcid.org/0000-0002-4077-4719] comment: This is also sometimes known as the Gattermann reaction. Also doesn't work to make fluorides or iodides. synonym: "Gattermann reaction" RELATED [] is_a: MOP:0000550 ! halogenation is_a: RXNO:0000332 ! aromatic substitution step union_of: RXNO:0000421 ! Gattermann chlorination union_of: RXNO:0000422 ! Gattermann bromination relationship: RXNO:0000425 CHEBI:28694 ! has_catalyst copper atom [Term] id: RXNO:0000023 name: Koerner-Contardi reaction def: "An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(II) halide to form an aromatic halide." [http://orcid.org/0000-0002-4077-4719] is_a: RXNO:0000332 ! aromatic substitution step [Term] id: RXNO:0000024 name: Heck reaction def: "A carbon-carbon coupling reaction where an organohalide or triflate couples to a terminal olefin to produce an internal olefin, catalysed by palladium. It is stereospecific." [http://orcid.org/0000-0001-5985-7429, RSC:db] comment: This usually produces the trans-olefin rather than the cis-. ALSO Merck Index gives a non-terminal example. synonym: "Heck-Mizoroki reaction" EXACT [] synonym: "Mizoroki-Heck reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/r192/ xref: NAMERXN:3.2 intersection_of: RXNO:0000624 intersection_of: RXNO:0000425 CHEBI:33363 ! has_catalyst palladium [Term] id: RXNO:0000025 name: rearrangement step def: "A reaction which preserves the number of rings and number of skeletal atoms and in which the molecule rearranges so that one or more atoms or groups of atoms move from one atom to another." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000001 ! planned reaction step intersection_of: RXNO:0000001 ! planned reaction step intersection_of: OBI:0000417 RXNO:0000441 ! achieves_planned_objective molecular rearrangement objective relationship: OBI:0000417 RXNO:0000441 ! achieves_planned_objective molecular rearrangement objective [Term] id: RXNO:0000026 name: Beckmann rearrangement def: "A rearrangement where an oxime rearranges to form an amide. Often there is selective migration of one group." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000029 is_a: RXNO:0000025 ! rearrangement step relationship: RXNO:0000423 CHEBI:32988 ! has specified product amide relationship: RXNO:0000424 CHEBI:25750 ! has specified reactant oxime [Term] id: RXNO:0000028 name: Cope rearrangement def: "A [3,3]-sigmatropic rearrangement where a 1,5-hexadiene rearranges to form a 1,5-hexadiene." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000086/ is_a: MOP:0000721 ! [3,3]-sigmatropic rearrangement is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000029 name: oxy-Cope rearrangement def: "A [3,3]-sigmatropic rearrangement of a 3-hydroxy-1,5-hexadiene rearranges to form a 5,6-unsaturated carbonyl compound." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/r86/ is_a: MOP:0000721 ! [3,3]-sigmatropic rearrangement is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000030 name: molecular skeleton insertion reaction def: "A joining reaction in which one or more atoms are added to the middle of a chain." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000000 ! molecular skeleton joining reaction intersection_of: RXNO:0000000 ! molecular skeleton joining reaction intersection_of: OBI:0000417 RXNO:0000487 ! achieves_planned_objective molecular skeleton insertion objective relationship: OBI:0000417 RXNO:0000487 ! achieves_planned_objective molecular skeleton insertion objective [Term] id: RXNO:0000031 name: Baeyer-Villiger oxidation alt_id: RXNO:0000190 def: "A reaction of a ketone to give an ester, in which an alkyl, benzyl or phenyl group migrates from one of the alpha-carbon centres to an adjacent oxygen, displacing an oxygen-based leaving group; the result is a formal insertion of an oxygen atom. The reaction also works with aldehydes, giving the corresponding carboxylic acid. The term \"Baeyer-Villiger rearrangement\" may occasionally be used in a mechanistic sense to refer specificially to the actual rearrangement step." [http://orcid.org/0000-0002-4077-4719, rsc:db] synonym: "B-V reaction" EXACT [] synonym: "Baeyer-Villiger oxidative rearrangement" EXACT [] synonym: "Baeyer-Villiger reaction" EXACT [] synonym: "Baeyer-Villiger rearrangement" RELATED [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000013/ is_a: RXNO:0000030 ! molecular skeleton insertion reaction relationship: RXNO:0000423 CHEBI:33308 ! has specified product carboxylic ester relationship: RXNO:0000424 CHEBI:17087 ! has specified reactant ketone [Term] id: RXNO:0000032 name: Mannich reaction def: "A carbon-carbon coupling reaction where ammonia or an amine reacts with a non-enolisable aldehyde, often methanal, and an enolisable carbonyl compound to form a beta-amino carbonyl compound." [RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000265/ is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: RXNO:0000424 MOP:0000718 ! has specified reactant enolisable carbonyl compound [Term] id: RXNO:0000034 name: Mitsunobu reaction def: "A substitution where an alcohol is converted into something else. Typical reagents are a dialkyl azodicarboxylate and a triarylphosphine. The alcohol stereocentre is inverted." [http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000287/ is_a: RXNO:0000331 ! substitution step relationship: RXNO:0000424 CHEBI:30879 ! has specified reactant alcohol [Term] id: RXNO:0000035 name: Stille coupling def: "A carbon-carbon coupling reaction where a stannane reacts with an organohalide or organotriflate." [RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000415/ xref: NAMERXN:3.4 is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: RXNO:0000424 CHEBI:25717 ! has specified reactant organotin compound [Term] id: RXNO:0000036 name: Reformatsky reaction def: "A carbon-carbon coupling reaction where an aldehyde or amine reacts with a alpha-halo ester and zinc to form a beta-hydroxy ester." [http://orcid.org/0000-0001-5985-7429] synonym: "Reformatskii reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000361/ is_a: RXNO:0000002 ! carbon-carbon coupling reaction relationship: has_part MOP:0000580 ! ketone reduction relationship: has_part MOP:0001550 ! dehalogenation [Term] id: RXNO:0000037 name: functional group reduction def: "A functional group modification reaction where a functional group is reduced." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000011 ! functional group modification intersection_of: RXNO:0000011 ! functional group modification intersection_of: OBI:0000417 RXNO:0000455 ! achieves_planned_objective functional reduction objective relationship: OBI:0000417 RXNO:0000455 ! achieves_planned_objective functional reduction objective [Term] id: RXNO:0000038 name: Clemmensen reduction def: "A functional group reduction where an aldehyde or ketone carbonyl group is reduced to a methylene with zinc-mercury amalgam and hydrochloric acid." [RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000082/ is_a: RXNO:0000037 ! functional group reduction [Term] id: RXNO:0000039 name: carbon-carbon homocoupling reaction def: "A joining reaction where a carbon-carbon bond is formed between like moieties." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000002 ! carbon-carbon coupling reaction [Term] id: RXNO:0000040 name: Ullmann reaction def: "A carbon-carbon homocoupling reaction of an aryl halide mediated by copper." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000441/ is_a: RXNO:0000039 ! carbon-carbon homocoupling reaction [Term] id: RXNO:0000041 name: addition reaction step def: "A reaction in which two or more groups of atoms are added to the molecule, resulting in a change of skeletal bond order." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000011 ! functional group modification intersection_of: RXNO:0000010 ! functional modification intersection_of: OBI:0000417 RXNO:0000456 ! achieves_planned_objective addition objective relationship: OBI:0000417 RXNO:0000456 ! achieves_planned_objective addition objective [Term] id: RXNO:0000042 name: Birch reduction def: "Addition of hydrogen atoms to aromatic rings by means of alkali metals in liquid ammonia." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000044/ is_a: RXNO:0000041 ! addition reaction step [Term] id: RXNO:0000043 name: Claisen condensation def: "A carbon-carbon coupling reaction of an ester and a carbonyl compound to form a beta-keto ester." [http://orcid.org/0000-0002-4077-4719] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000079/ is_a: MOP:0000723 ! deethanolative condensation is_a: RXNO:0000000 ! molecular skeleton joining reaction [Term] id: RXNO:0000044 name: Knoevenagel condensation def: "A carbon-carbon coupling reaction of an aldehyde and a methylene compound." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000230/ is_a: MOP:0000722 ! decarboxylative condensation is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde [Term] id: RXNO:0000045 name: Friedel-Crafts acylation def: "A carbon-carbon coupling reaction between an arene and a carbonyl compound (usually an acyl halide) to give an aryl ketone. The reaction is catalysed by a Lewis acid." [http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000158/ is_a: RXNO:0000369 ! Friedel-Crafts reaction relationship: has_part MOP:0000734 ! Lewis acid catalysis [Term] id: RXNO:0000046 name: Friedel-Crafts alkylation def: "A carbon-carbon coupling reaction between an arene and an alkyl halide/alkene/alcohol (anything that can form a carbocation) to give a substituted arene. The reaction is catalysed by a Lewis acid." [http://orcid.org/0000-0002-4077-4719, RSC:db] comment: It proceeds by an SN1 mechanism. xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000158/ is_a: RXNO:0000369 ! Friedel-Crafts reaction relationship: has_part MOP:0000734 ! Lewis acid catalysis [Term] id: RXNO:0000047 name: Oppenauer oxidation def: "An oxidation of a secondary alcohol to a ketone involving an equilibrium between the alcohol and a reagent ketone present in excess, catalysed by a metal alkoxide." [http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000311/ is_a: RXNO:0000012 ! functional group oxidation relationship: RXNO:0000423 CHEBI:17478 ! has specified product aldehyde relationship: RXNO:0000424 CHEBI:35681 ! has specified reactant secondary alcohol relationship: RXNO:0000424 CHEBI:17087 relationship: RXNO:0000425 CHEBI:33521 [Term] id: RXNO:0000048 name: Prins reaction def: "A carbon-carbon coupling between formaldehyde and an alkene to give a 1,3-diol or an allylic alcohol, catalysed by acid." [http://orcid.org/0000-0002-4077-4719, RSC:db] comment: See also "intramolecular Prins reaction". xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000352/ is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: has_part MOP:0000730 ! Brønsted acid catalysis relationship: RXNO:0000424 CHEBI:16842 ! has specified reactant formaldehyde [Term] id: RXNO:0000049 name: intramolecular Prins reaction def: "A reaction between formaldehyde and an alkene to give a 1,3-dioxane, catalysed by acid." [http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000352/ is_a: RXNO:0000005 ! ring formation reaction step relationship: has_part MOP:0000730 ! Brønsted acid catalysis relationship: RXNO:0000424 CHEBI:16842 ! has specified reactant formaldehyde [Term] id: RXNO:0000050 name: pinacol rearrangement def: "A rearrangement of a 1,2-diol to give a carbonyl compound, catalysed by acid." [http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000341/ is_a: RXNO:0000025 ! rearrangement step relationship: has_part MOP:0000730 ! Brønsted acid catalysis [Term] id: RXNO:0000051 name: Wolff rearrangement def: "A rearrangement of a diazoketone to give a ketene, with the elimination of molecular nitrogen." [http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000474/ is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000052 name: fused-ring-system formation def: "A reaction in which a fused ring system is present in a product that was not present in any of the reactants." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000005 ! ring formation reaction step intersection_of: MOP:0000543 ! molecular process intersection_of: RXNO:0000423 CHEBI:35293 ! has specified product fused compound relationship: OBI:0000417 RXNO:0000465 ! achieves_planned_objective fused-ring-system formation objective relationship: RXNO:0000423 CHEBI:35293 ! has specified product fused compound [Term] id: RXNO:0000053 name: Bischler-Napieralski reaction def: "A cyclodehydration of a beta-phenethylamide to give a 3,4-dihydroisoquinoline." [http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Bischler-Napieralski 3,4-dihydroisoquinoline synthesis" EXACT [] synonym: "Bischler-Napieralski dihydroisoquinoline synthesis" EXACT [] synonym: "Bischler-Napieralski isoquinoline synthesis" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000046/ is_a: RXNO:0000052 ! fused-ring-system formation [Term] id: RXNO:0000054 name: Curtius rearrangement def: "A rearrangement of an acyl azide to give an isocyanate by pyrolysis, with the elimination of molecular nitrogen." [http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Curtius reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000097/ is_a: RXNO:0000025 ! rearrangement step relationship: RXNO:0000423 CHEBI:53212 relationship: RXNO:0000424 CHEBI:22680 [Term] id: CHEBI:53212 name: isocyanates is_a: CHEBI:35352 [Term] id: CHEBI:22680 name: azide is_a: CHEBI:35352 [Term] id: RXNO:0000055 name: Vilsmeier-Haack reaction def: "A formylation of an activated arene with a disubstituted formamide to give an arenecarbaldehyde." [http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Vilsmeier-Haack formylation" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000444/ is_a: MOP:0000003 ! formylation is_a: RXNO:0000002 ! carbon-carbon coupling reaction relationship: RXNO:0000423 CHEBI:33855 relationship: RXNO:0000424 CHEBI:33658 relationship: RXNO:0000424 CHEBI:24079 [Term] id: CHEBI:24079 name: formamides is_a: CHEBI:35636 [Term] id: CHEBI:33855 name: arenecarbaldehyde is_a: CHEBI:33658 ! arene [Term] id: CHEBI:33658 name: arene is_a: CHEBI:72695 [Term] id: CHEBI:37592 name: organic phosphonate is_a: CHEBI:25710 ! organophosphorus compound [Term] id: CHEBI:25710 name: organophosphorus compound is_a: CHEBI:23367 [Term] id: RXNO:0000056 name: Horner-Wadsworth-Emmons reaction def: "A carbon-carbon coupling reaction between a phosphonate and a carbonyl compound to give an olefin." [http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Emmons reaction" EXACT [] synonym: "Horner-Emmons reaction" EXACT [] synonym: "Horner-Emmons-Wadsworth reaction" EXACT [] synonym: "Horner-Wadsworth-Emmons (HWE) olefination" EXACT [] synonym: "Horner-Wadsworth-Emmons olefination" EXACT [] synonym: "Horner-Wittig reaction" EXACT [] synonym: "Wadsworth-Emmons olefination" EXACT [] synonym: "Wadsworth-Emmons reaction" EXACT [] synonym: "Wadsworth-Emmons-Horner reaction" EXACT [] synonym: "Wittig-Horner reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000468/ is_a: RXNO:0000479 ! olefination relationship: RXNO:0000423 CHEBI:33641 ! has specified product olefin relationship: RXNO:0000424 CHEBI:36587 ! has specified reactant carbonyl compound relationship: RXNO:0000424 CHEBI:37592 ! has specified reactant organic phosphonate [Term] id: RXNO:0000057 name: Horner reaction def: "A joining reaction between a phosphine oxide and a carbonyl compound to give an olefin." [http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000468/ is_a: RXNO:0000479 ! olefination relationship: OBI:0000417 RXNO:0000440 ! achieves_planned_objective molecular skeleton joining objective relationship: RXNO:0000423 CHEBI:33641 ! has specified product olefin relationship: RXNO:0000424 CHEBI:36587 ! has specified reactant carbonyl compound relationship: RXNO:0000424 CHEBI:59656 ! has specified reactant phosphine oxide [Term] id: RXNO:0000058 name: Ritter reaction def: "A reaction between an alcohol or alkene and a nitrile to give an amide, catalysed by a Bronsted acid." [http://orcid.org/0000-0002-4077-4719, RSC:db] comment: Proceeds by an SN1 mechanism. xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000372/ is_a: RXNO:0000011 ! functional group modification relationship: has_part MOP:0000730 ! Brønsted acid catalysis [Term] id: RXNO:0000059 name: Pictet-Spengler reaction def: "A condensation-cyclisation of a beta-phenethylamine with an aldehyde to give a tetrahydroisoquinoline." [http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Pictet-Spengler isoquinoline synthesis" EXACT [] synonym: "Pictet-Spengler tetrahydroisoquinoline synthesis" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000338/ is_a: MOP:0000627 ! condensation reaction is_a: RXNO:0000052 ! fused-ring-system formation relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde [Term] id: RXNO:0000060 name: Arbuzov reaction alt_id: RXNO:0000112 def: "The alkylation of a trialkyl phosphite with an alkyl halide or acyl halide to give an alkyl phosphonate." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Michaelis-Arbuzov phosphonate synthesis" EXACT [] synonym: "Michaelis-Arbuzov reaction" EXACT [] is_a: RXNO:0000331 ! substitution step relationship: has_part MOP:0000719 ! O-dealkylation relationship: has_part MOP:0006369 ! P-alkylation [Term] id: RXNO:0000061 name: Mukaiyama aldol condensation def: "An aldol condensation between an aldehyde or ketone and a silyl enol ether (also known as a ketene silyl acetal) to give a beta-hydroxy carbonyl compound." [http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Mukaiyama aldol reaction" EXACT [] is_a: RXNO:0000017 ! aldol condensation [Term] id: RXNO:0000062 name: Skraup reaction def: "A condensation between an aromatic amine and glycerol to give a quinoline." [http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Skraup quinoline synthesis" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000403/ is_a: MOP:0000628 ! molecular dehydration reaction is_a: RXNO:0000393 ! quinoline synthesis relationship: RXNO:0000423 CHEBI:26513 ! has specified product quinolines relationship: RXNO:0000424 CHEBI:33860 ! has specified reactant aromatic amine [Term] id: RXNO:0000063 name: Arndt-Eistert reaction def: "A homologation reaction of a carboxylic acid to give the homologated carboxylic acid via acyl chloride and diazoketone intermediates." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] comment: This is an insertion because the carbon atom is added between the R group and the carboxyl carbon in the starting material. synonym: "Arndt-Eistert synthesis" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000010/ is_a: RXNO:0000030 ! molecular skeleton insertion reaction relationship: RXNO:0000423 CHEBI:33575 ! has specified product carboxylic acid relationship: RXNO:0000424 CHEBI:33575 ! has specified reactant carboxylic acid relationship: RXNO:0000469 CHEBI:36687 ! has_intermediate acyl chloride [Term] id: RXNO:0000064 name: Fischer indole synthesis def: "Reaction of an aldehyde or ketone with a phenylhydrazine to give an indole." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Fischer indolisation" EXACT [] synonym: "Fischer indolization" EXACT [] is_a: RXNO:0000395 ! indole synthesis relationship: RXNO:0000424 CHEBI:25996 ! has specified reactant phenylhydrazine [Term] id: RXNO:0000065 name: Dieckmann cyclisation def: "An intramolecular cyclisation of a diester to give a cyclic beta-ketoester." [http://orcid.org/0000-0002-4077-4719, RSC:db] comment: This is the intramolecular version of the Claisen condensation. synonym: "Dieckmann condensation" EXACT [] synonym: "Dieckmann cyclization" EXACT [] synonym: "Dieckmann reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000108/ is_a: MOP:0000723 ! deethanolative condensation is_a: RXNO:0000005 ! ring formation reaction step [Term] id: RXNO:0000066 name: Staudinger reaction def: "A joining of an organic azide and a tertiary phosphine to give a phosphazo compound." [http://orcid.org/0000-0002-4077-4719, RSC:db] comment: Hydrolysis of the phosphazo compound gives the corresponding amine." [http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Staudinger ligation" EXACT [] synonym: "Staudinger reduction" EXACT [] is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: RXNO:0000424 CHEBI:35886 ! has specified reactant tertiary phosphine [Term] id: RXNO:0000067 name: benzidine rearrangement def: "A rearrangement of a hydrazobenzene to give a diaminobiphenyl compound." [http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000033/ is_a: RXNO:0000093 ! extrusion reaction [Term] id: RXNO:0000068 name: semidine rearrangement def: "A rearrangement of a p-substituted hydrazobenzene to give a p-aminodiphenylamine." [http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000033/ is_a: RXNO:0000093 ! extrusion reaction [Term] id: RXNO:0000069 name: Dimroth rearrangement def: "A rearrangement of a heterocyclic compound in which endocyclic and exocyclic heteroatoms swap places." [http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000111/ is_a: RXNO:0000202 ! ring rearrangement [Term] id: RXNO:0000070 name: chain lengthening def: "A molecular skeleton joining reaction in which a chain part of a molecular skeleton is lengthened." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000000 ! molecular skeleton joining reaction intersection_of: RXNO:0000000 ! molecular skeleton joining reaction intersection_of: OBI:0000417 RXNO:0000448 ! achieves_planned_objective molecular chain lengthening objective relationship: OBI:0000417 RXNO:0000448 ! achieves_planned_objective molecular chain lengthening objective [Term] id: RXNO:0000071 name: Edman degradation def: "A cleaving reaction in which a peptide is treated with phenylisothiocyanate, removing the terminal amino acid group, to form the chain-shortened amine and a phenylthiohydantoin." [http://orcid.org/0000-0002-4077-4719, RSC:db] comment: The latter can be used to identify the terminal amino acid, and the process repeated to enable peptide sequencing." xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000122/ is_a: RXNO:0000517 ! terminal amino-acid residue cleaving reaction relationship: RXNO:0000423 CHEBI:32952 ! has specified product amine relationship: RXNO:0000424 CHEBI:16670 ! has specified reactant peptide [Term] id: RXNO:0000072 name: Reimer-Tiemann reaction def: "A formylation reaction between a phenol and chloroform (for example, to form an ortho-formyl phenol)." [http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: MOP:0000003 ! formylation is_a: RXNO:0000002 ! carbon-carbon coupling reaction xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000362/ relationship: RXNO:0000423 CHEBI:33853 relationship: RXNO:0000424 CHEBI:35255 [Term] id: CHEBI:33853 name: phenols is_a: CHEBI:72695 [Term] id: RXNO:0000073 name: cleaving reaction def: "A reaction where atoms are lost from the molecular skeleton." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000001 ! planned reaction step intersection_of: RXNO:0000001 ! planned reaction step intersection_of: OBI:0000417 RXNO:0000438 ! achieves_planned_objective molecular skeleton cleaving objective relationship: OBI:0000417 RXNO:0000438 ! achieves_planned_objective molecular skeleton cleaving objective [Term] id: RXNO:0000074 name: Wurtz reaction def: "A carbon-carbon homocoupling reaction of two molecules of an alkyl halide with sodium to give a symmetrical product." [http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Wurtz coupling" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000478/ is_a: RXNO:0000039 ! carbon-carbon homocoupling reaction [Term] id: RXNO:0000075 name: benzilic acid rearrangement def: "A rearrangement of a 1,2-diketone to an alpha-hydroxy carboxylic acid. It can also be applied to alpha-keto aldehydes. The first exmaple of this reaction was with benzil (PhC(=O)C(=O)Ph) to form benzilic acid, hence the name." [http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000034/ is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000076 name: Baylis-Hillman reaction def: "A carbon-carbon coupling of an aldehyde to an activated alkene in the presence of a nucleophilic base to give an alpha-hydroxyalkylated compound." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "MBH reaction" EXACT [] synonym: "Morita-Baylis-Hillman reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000027/ is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde [Term] id: RXNO:0000077 name: Darzens reaction def: "A coupling of an aldehyde or ketone with an alpha-halo ester to form an alpha,beta-epoxy ester, which hydrolyses to yield aldehydes or ketones by elimination of carbon dioxide." [http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Darzens condensation" EXACT [] synonym: "Darzens-Claisen reaction" EXACT [] synonym: "glycidic ester condensation" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000101/ is_a: MOP:0000722 ! decarboxylative condensation is_a: RXNO:0000000 ! molecular skeleton joining reaction [Term] id: RXNO:0000078 name: protection reaction def: "A reaction in which a functional group is modified by converting it into a protecting group, in order to make subsequent reactions more selective." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:5 is_a: RXNO:0000010 ! functional modification intersection_of: RXNO:0000010 ! functional modification intersection_of: RXNO:0000416 CHEBI:24433 ! protects group disjoint_from: RXNO:0000203 ! deprotection reaction relationship: part_of RXNO:0000329 ! planned synthesis relationship: RXNO:0000416 CHEBI:24433 ! protects group [Term] id: RXNO:0000079 name: Boc protection def: "A protection reaction in which an amine is converted into a tert-butoxycarbonyl compound." [http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000321 ! amino group protection relationship: RXNO:0000416 CHEBI:46882 ! protects amino group relationship: RXNO:0000424 CHEBI:32952 ! has specified reactant amine [Term] id: RXNO:0000080 name: Peterson olefination def: "A carbon-carbon coupling reaction in which an alpha-silyl carbanion reacts with an aldehyde or a ketone to give an alkene, proceeding via a beta-hydroxysilane. The stereochemistry of the alkene can be controlled by treating the intermediate with acid or base." [http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Peterson reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000331/ is_a: RXNO:0000479 ! olefination relationship: RXNO:0000423 CHEBI:33641 ! has specified product olefin [Term] id: RXNO:0000081 name: Ullmann condensation def: "A coupling reaction in which a phenol is coupled to an aryl halide to give a diaryl ether in the presence of a copper compound." [http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Ullmann ether synthesis" EXACT [] is_a: RXNO:0000332 ! aromatic substitution step [Term] id: RXNO:0000082 name: Goldberg reaction def: "A coupling reaction in which an acetanilide is coupled to an aryl halide to give an N-acetyl diaryl amine in the presence of a copper compound." [http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000332 ! aromatic substitution step [Term] id: RXNO:0000083 name: Paternò–Büchi reaction def: "A photochemical cycloaddition between an aldehyde or ketone and an alkene to give an oxetane." [http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Paterno-Buchi reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000319/ is_a: MOP:0000563 ! [2+2] cycloaddition is_a: RXNO:0000346 ! oxacycle synthesis relationship: RXNO:0000423 CHEBI:38784 ! has specified product oxetanes [Term] id: RXNO:0000084 name: Barbier reaction def: "A joining reaction between an aldehyde or ketone and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a secondary or tertiary alcohol." [http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000000 ! molecular skeleton joining reaction union_of: RXNO:0000426 ! aldehyde Barbier reaction union_of: RXNO:0000427 ! ketone Barbier reaction [Term] id: RXNO:0000085 name: acyloin condensation def: "A reductive coupling reaction between two esters to give an acyloin (an alpha-hydroxyketone)." [http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000002/ is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: has_part MOP:0000627 ! condensation reaction relationship: RXNO:0000424 CHEBI:33308 ! has specified reactant carboxylic ester [Term] id: RXNO:0000086 name: Henry reaction def: "A carbon-carbon coupling reaction between a nitroalkane and an aldehyde or ketone to give a beta-hydroxy nitroalkane." [http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "nitroaldol reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/r196/ is_a: RXNO:0000002 ! carbon-carbon coupling reaction [Term] id: RXNO:0000087 name: Barton reaction def: "The photolytic oxidation of a nitrate ester to give a gamma-nitroalcohol." [http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000024/ is_a: RXNO:0000025 ! rearrangement step relationship: RXNO:0000424 CHEBI:51080 ! has specified reactant nitrate ester [Term] id: CHEBI:32863 name: secondary amine is_a: CHEBI:32952 [Term] id: CHEBI:35255 name: chloroform is_a: CHEBI:72695 [Term] id: CHEBI:73474 name: acetylenic compound is_a: CHEBI:72695 [Term] id: CHEBI:72695 name: organic molecule is_a: CHEBI:23367 [Term] id: RXNO:0000088 name: Negishi coupling def: "A carbon-carbon coupling reaction between an organohalide or organotriflate and an organozinc compound. The reaction is catalysed by palladium or nickel." [http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Negishi cross-coupling" EXACT [] xref: https://en.wikipedia.org/wiki/Negishi_coupling xref: https://www.rsc.org/Merck-Index/reaction/r299/ is_a: RXNO:0000002 ! carbon-carbon coupling reaction [Term] id: RXNO:0000089 name: Meerwein-Ponndorf-Verley reduction def: "A reduction of an aldehyde or ketone to an alcohol involving an equilibrium between the aldehyde or ketone and a reagent alcohol present in excess, catalysed by a metal alkoxide. This reaction is the reverse of the Oppenauer oxidation (RXNO:0000047)." [http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://en.wikipedia.org/wiki/Meerwein%E2%80%93Ponndorf%E2%80%93Verley_reduction xref: https://www.rsc.org/Merck-Index/reaction/r272/ is_a: RXNO:0000037 union_of: RXNO:0000622 union_of: RXNO:0000623 relationship: RXNO:0000424 CHEBI:30879 [Term] id: RXNO:0000090 name: Williamson ether synthesis def: "The reaction between an alkyl halide or alkyl sulfate and a metal alkoxide to give an ether." [http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Williamson etherification" EXACT [] is_a: RXNO:0000331 ! substitution step [Term] id: RXNO:0000091 name: Wittig methylenation def: "A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give a terminal alkene." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000015 ! Wittig reaction [Term] id: RXNO:0000092 name: aza-Diels-Alder reaction def: "A Diels-Alder reaction between a diene and an imine or an azadiene and an alkene to give a six-membered nitrogen-containing ring compound." [http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "aza-Diels-Alder cycloaddition" EXACT [] synonym: "aza Diels-Alder cycloaddition" EXACT [] synonym: "azo-Diels-Alder cycloaddition" EXACT [] synonym: "azo Diels-Alder cycloaddition" EXACT [] synonym: "aza Diels-Alder reaction" EXACT [] synonym: "azo-Diels-Alder reaction" EXACT [] synonym: "azo Diels-Alder reaction" EXACT [] is_a: RXNO:0000313 ! hetero-Diels-Alder reaction [Term] id: RXNO:0000093 name: extrusion reaction def: "A cleaving reaction in which a skeletal atom or group of atoms is removed from the middle of a molecule." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000073 ! cleaving reaction intersection_of: RXNO:0000073 ! cleaving reaction intersection_of: OBI:0000417 RXNO:0000462 ! achieves_planned_objective molecular extrusion objective relationship: OBI:0000417 RXNO:0000462 ! achieves_planned_objective molecular extrusion objective [Term] id: RXNO:0000094 name: Ramberg-Backlund reaction def: "The reaction of an alpha-halosulfone to give an alkene, with the extrusion of sulfur dioxide." [http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000093 ! extrusion reaction [Term] id: RXNO:0000095 name: Fischer-Hepp rearrangement def: "The rearrangement of an aromatic nitrosamine to a para-nitrosoaniline." [http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000096 name: azo coupling def: "A coupling reaction of a diazonium salt with a phenol or aniline to give an azo compound." [http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000011 ! functional group modification [Term] id: RXNO:0000097 name: imino-Reformatsky reaction def: "A carbon-carbon coupling reaction where an imine reacts with a alpha-halo ester and zinc to form a beta-amino ester." [http://orcid.org/0000-0001-5985-7429] synonym: "imino Reformatsky reaction" EXACT [] is_a: RXNO:0000036 ! Reformatsky reaction [Term] id: RXNO:0000098 name: Glaser coupling def: "A coupling reaction between two molecules of a terminal alkyne catalysed by Cu(I) salts." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000000 ! molecular skeleton joining reaction is_a: RXNO:0000039 ! carbon-carbon homocoupling reaction relationship: RXNO:0000424 CHEBI:73477 ! has specified reactant terminal acetylenic compound [Term] id: RXNO:0000099 name: Eglinton reaction def: "A coupling reaction between two molecules of a terminal alkyne using stoichiometric Cu(II) salts." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Eglinton coupling" EXACT [] is_a: RXNO:0000000 ! molecular skeleton joining reaction is_a: RXNO:0000039 ! carbon-carbon homocoupling reaction relationship: RXNO:0000424 CHEBI:73477 ! has specified reactant terminal acetylenic compound [Term] id: RXNO:0000100 name: Cadiot-Chodkiewicz coupling def: "A coupling reaction between a terminal alkyne and an alkynyl halide catalysed by Cu(I) salts." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: RXNO:0000424 CHEBI:73477 ! has specified reactant terminal acetylenic compound [Term] id: RXNO:0000101 name: Leuckart reaction def: "The reductive amination of ketones or aldehydes with an ammonium formate or formamide to form an amine." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000335 ! reductive amination union_of: RXNO:0000552 ! Leuckart aldehyde reaction union_of: RXNO:0000553 ! Leuckart ketone reaction [Term] id: RXNO:0000102 name: Leuckart-Wallach reaction def: "The reductive amination of ketones or aldehydes with an amine and formic acid to form amines." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Wallach reaction" EXACT [] is_a: RXNO:0000335 ! reductive amination [Term] id: RXNO:0000103 name: Gabriel synthesis def: "The reaction of primary alkyl halides with sodium or potassium phthalimide, followed by hydrolysis, to give the corresponding primary amine." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000331 ! substitution step [Term] id: RXNO:0000104 name: Ing-Manske procedure def: "The reaction of primary alkyl halides with sodium or potassium phthalimide, followed by treatment with hydrazine, to give the corresponding primary amine." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000331 ! substitution step [Term] id: RXNO:0000105 name: end-of-chain chain shortening def: "A reaction in which a single skeletal atom is removed from the end of a chain." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000073 ! cleaving reaction intersection_of: RXNO:0000073 ! cleaving reaction intersection_of: OBI:0000417 RXNO:0000454 ! achieves_planned_objective end-of-chain chain shortening objective relationship: OBI:0000417 RXNO:0000454 ! achieves_planned_objective end-of-chain chain shortening objective [Term] id: RXNO:0000106 name: Hunsdiecker reaction def: "The decarboxylation of silver carboxylates with halogens to give organic halides." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Borodin reaction" EXACT [] synonym: "Borodine reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000215/ is_a: RXNO:0000105 ! end-of-chain chain shortening [Term] id: RXNO:0000107 name: malonic ester synthesis def: "A carbon-carbon coupling reaction between a dialkyl malonate and an alkyl halide, to give a substituted acetic acid. The base/R'X treatment can be repeated to give a disubstituted product." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000264/ is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: OBI:0000417 RXNO:0000440 ! achieves_planned_objective molecular skeleton joining objective relationship: RXNO:0000423 CHEBI:33575 ! has specified product carboxylic acid relationship: RXNO:0000424 CHEBI:24469 ! has specified reactant haloalkane [Term] id: RXNO:0000108 name: ring expansion def: "A reaction in which an existing ring is increased in size." [http://orcid.org/0000-0001-5985-7429] synonym: "ring enlargement" EXACT [] is_a: RXNO:0000005 ! ring formation reaction step relationship: OBI:0000417 RXNO:0000457 ! achieves_planned_objective molecular ring expansion objective [Term] id: RXNO:0000109 name: Pfitzinger reaction def: "The reaction between isatin and an alpha-methylene carbonyl compound to give a substituted quinoline-4-carboxylic acid." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Pfitzinger quinoline synthesis" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000334/ is_a: RXNO:0000108 ! ring expansion [Term] id: RXNO:0000110 name: fragmentation reaction def: "A reaction in which the parent molecule breaks up into three or more products." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000073 ! cleaving reaction intersection_of: RXNO:0000073 ! cleaving reaction intersection_of: OBI:0000417 RXNO:0000463 ! achieves_planned_objective molecular fragmentation objective relationship: OBI:0000417 RXNO:0000463 ! achieves_planned_objective molecular fragmentation objective [Term] id: RXNO:0000111 name: Grob fragmentation def: "The fragmentation of a molecule that takes place when an electron-donating fragment (X) and an electron-accepting fragment (X') are situated at positions 1 and 3 on an aliphatic chain, to give a cationic fragment, a neutral fragment (e.g. an alkene) and an anionic fragment." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000110 ! fragmentation reaction [Term] id: RXNO:0000113 name: Brook rearrangement def: "The rearrangement of an alpha-, beta- or gamma-hydroxy silane to give a silyl ether. It is catalysed by a base." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000062/ is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000114 name: Nicholas reaction def: "The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a nucleophile to give a substituted alkyne." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000303/ is_a: RXNO:0000331 ! substitution step union_of: RXNO:0000115 ! Nicholas reaction, nucleophilic heteroatom centre union_of: RXNO:0000116 ! Nicholas reaction, nucleophilic carbon centre [Term] id: RXNO:0000115 name: Nicholas reaction, nucleophilic heteroatom centre def: "The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a hydride or amine or enamine to give a substituted alkyne." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000114 ! Nicholas reaction [Term] id: RXNO:0000116 name: Nicholas reaction, nucleophilic carbon centre def: "The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a nucleophilic carbon centre (on e.g. enolates, allyl silanes, ketones, electron-rich aromatics, beta-dicarbonyl compounds) to give a substituted alkyne." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000002 ! carbon-carbon coupling reaction is_a: RXNO:0000114 ! Nicholas reaction [Term] id: RXNO:0000117 name: Julia olefination def: "A carbon-carbon coupling reaction between a phenyl sulfone and an aldehyde or ketone to give a (typically trans) alkene." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Julia-Lythgoe olefination" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000224/ is_a: RXNO:0000479 ! olefination relationship: RXNO:0000423 CHEBI:33641 ! has specified product olefin [Term] id: RXNO:0000118 name: Sommelet reaction def: "The oxidation of a benzylic halide to give an aldehyde. The reaction uses hexamethylenetetramine." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000011 ! functional group modification relationship: RXNO:0000423 CHEBI:17478 ! has specified product aldehyde [Term] id: RXNO:0000119 name: Bouveault-Blanc reaction def: "The reduction of an ester using sodium to give two alcohols." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Bouveault-Blanc procedure" EXACT [] synonym: "Bouveault-Blanc reduction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000058/ is_a: RXNO:0000037 ! functional group reduction relationship: RXNO:0000423 CHEBI:30879 ! has specified product alcohol relationship: RXNO:0000424 CHEBI:26708 ! has specified reactant sodium atom relationship: RXNO:0000424 CHEBI:33308 ! has specified reactant carboxylic ester [Term] id: RXNO:0000120 name: Payne rearrangement def: "A base-catalysed isomerisation of a 2,3-epoxyalcohol, with inversion of configuration at C2." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000321/ is_a: RXNO:0000202 ! ring rearrangement [Term] id: RXNO:0000121 name: aza-Payne rearrangement def: "A base-catalysed isomerisation of a 2,3-epoxyamine to form a hydroxy aziridine, with inversion of configuration at C2." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000321/ is_a: RXNO:0000202 ! ring rearrangement [Term] id: RXNO:0000122 name: Baker-Venkataraman rearrangement def: "The base-catalysed rearrangement of an o-acetoxyacetophenone to give a hydroxyphenyl-1,3-diketone." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000014/ is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000123 name: molecular skeleton elimination reaction def: "A reaction in which two or more groups of atoms are removed from the molecule, resulting in a change of skeletal bond order." [http://orcid.org/0000-0001-5985-7429] comment: This is narrower in focus than elimination in general in that we're focussing on the aims of the chemist. is_a: RXNO:0000010 ! functional modification intersection_of: RXNO:0000010 ! functional modification intersection_of: OBI:0000417 RXNO:0000486 ! achieves_planned_objective molecular skeleton elimination objective relationship: OBI:0000417 RXNO:0000486 ! achieves_planned_objective molecular skeleton elimination objective [Term] id: RXNO:0000124 name: Bamford-Stevens reaction def: "The reaction of a tosylhydrazone of an aldehyde or ketone with a strong base to give an olefin." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] comment: This generally provides the more-substituted olefin as the thermodynamic product. xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000016/ is_a: RXNO:0000123 ! molecular skeleton elimination reaction relationship: RXNO:0000423 CHEBI:33641 ! has specified product olefin [Term] id: RXNO:0000125 name: Shapiro reaction def: "The reaction of a tosylhydrazone of an aldehyde or ketone with an alkyllithium or Grignard reagent to give an olefin." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] comment: This generally provides the less-substituted olefin as the kinetic product. xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000016/ is_a: RXNO:0000123 ! molecular skeleton elimination reaction relationship: RXNO:0000423 CHEBI:33641 ! has specified product olefin [Term] id: RXNO:0000126 name: Doebner reaction def: "The reaction between an aromatic amine, an aldehyde and pyruvic acid on heating to give a quinoline 4-carboxylic acid (cinchoninic acid)." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000114/ is_a: RXNO:0000393 ! quinoline synthesis relationship: RXNO:0000423 CHEBI:26513 ! has specified product quinolines relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde relationship: RXNO:0000424 CHEBI:32816 ! has specified reactant pyruvic acid relationship: RXNO:0000424 CHEBI:33860 ! has specified reactant aromatic amine [Term] id: RXNO:0000127 name: Balz-Schiemann reaction def: "The conversion of an aromatic amine to the corresponding fluoride via the diazonium fluoroborate." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Schiemann reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000388/ is_a: RXNO:0000332 ! aromatic substitution step relationship: RXNO:0000423 CHEBI:50888 ! has specified product fluoroarene relationship: RXNO:0000424 CHEBI:33860 ! has specified reactant aromatic amine [Term] id: RXNO:0000128 name: Kolbe electrolysis def: "The decarboxylation and coupling of a carboxylate or mixture of carboxylates to give a dimer." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Kolbe electrolytic synthesis" EXACT [] synonym: "Kolbe electrosynthesis" EXACT [] synonym: "Kolbe reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000238 is_a: RXNO:0000002 ! carbon-carbon coupling reaction [Term] id: RXNO:0000129 name: Ugi reaction def: "Reaction of a ketone or aldehyde, amine, an isocyanide and carboxylic acid to form a bisamide." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "4CC" EXACT [] synonym: "Ugi four-component condensation" EXACT [] synonym: "Ugi-4CR" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000440/ is_a: MOP:0000628 ! molecular dehydration reaction is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: RXNO:0000424 CHEBI:32877 ! has specified reactant primary amine relationship: RXNO:0000424 CHEBI:33575 ! has specified reactant carboxylic acid [Term] id: RXNO:0000130 name: Wacker-Tsuji oxidation def: "The oxidation of a terminal alkene or ethene to a methyl ketone or acetaldehyde, catalysed by PdCl2 and CuCl2, and using molecular oxygen as the oxidant." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Wacker oxidation" EXACT [] synonym: "Wacker reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000452/ is_a: RXNO:0000012 ! functional group oxidation relationship: RXNO:0000424 CHEBI:15379 ! has specified reactant dioxygen relationship: RXNO:0000425 CHEBI:49553 ! has_catalyst copper(II) chloride relationship: RXNO:0000425 CHEBI:53434 ! has_catalyst palladium(II) chloride [Term] id: RXNO:0000131 name: Wacker process def: "The oxidation of ethene to acetaldehyde, catalysed by PdCl2 and CuCl2, and using molecular oxygen as the oxidant." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000130 ! Wacker-Tsuji oxidation [Term] id: RXNO:0000132 name: Monsanto process def: "The reaction of formaldehyde with methanol to form acetic acid, catalysed by a rhodium complex." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: RXNO:0000424 CHEBI:16842 ! has specified reactant formaldehyde [Term] id: RXNO:0000133 name: Cativa process def: "The reaction of formaldehyde with methanol to form acetic acid, catalysed by an iridium complex." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: RXNO:0000424 CHEBI:16842 ! has specified reactant formaldehyde [Term] id: RXNO:0000134 name: Barton-McCombie deoxygenation def: "The deoxygenation of an alcohol to the corresponding alkane using a thiochloroformate. It proceeds by a radical mechanism." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Barton deoxygenation" EXACT [] synonym: "Barton reduction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000022/ is_a: RXNO:0000037 ! functional group reduction [Term] id: RXNO:0000135 name: Barton decarboxylation def: "The decarboxylation of a carboxylic acid to the lower homologue alkane using a pyridine thione." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] comment: The reaction proceeds by a radical mechanism. xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000021/ is_a: RXNO:0000105 ! end-of-chain chain shortening [Term] id: RXNO:0000136 name: Rosenmund reduction def: "The hydrogenolysis of an acyl halide to the corresponding aldehyde, catalysed by palladium-on-barium sulfate." [http://orcid.org/0000-0002-4077-4719, rsc:db] synonym: "Rosenmund reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000375/ is_a: RXNO:0000037 ! functional group reduction relationship: RXNO:0000423 CHEBI:17478 ! has specified product aldehyde relationship: RXNO:0000424 CHEBI:37579 ! has specified reactant acyl halide relationship: RXNO:0000425 CHEBI:33363 ! has_catalyst palladium [Term] id: RXNO:0000137 name: Sonogashira coupling def: "A carbon-carbon coupling reaction where a terminal alkyne reacts with an aryl halide to give an aryl alkyne. It is catalysed by palladium." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Hagihara-Sonogashira coupling" EXACT [] synonym: "Sonogashira cross-coupling" EXACT [] synonym: "Sonogashira reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000408/ xref: NAMERXN:3.3 is_a: RXNO:0000000 ! molecular skeleton joining reaction is_a: RXNO:0000316 ! palladium-catalysed carbon-carbon coupling reaction relationship: RXNO:0000423 CHEBI:73477 ! has specified product terminal acetylenic compound relationship: RXNO:0000425 CHEBI:33363 ! has_catalyst palladium [Term] id: RXNO:0000138 name: benzoin condensation def: "A reaction between two aromatic aldehydes to give a benzoin (an alpha-hydroxyketone)." [http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000035/ is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde [Term] id: RXNO:0000139 name: Gattermann reaction def: "The formylation of an arene with hydrogen cyanide to give an aryl aldehyde or ketone." [http://orcid.org/0000-0002-4077-4719, RSC:db] comment: This is essentially a variant of the Friedel-Crafts acylation. is_a: MOP:0000003 ! formylation is_a: RXNO:0000002 ! carbon-carbon coupling reaction relationship: RXNO:0000424 CHEBI:33658 relationship: has_part MOP:0000734 ! Lewis acid catalysis [Term] id: RXNO:0000140 name: Suzuki-Miyaura coupling def: "The coupling of a boronic acid or boronic ester with an unsaturated halide, triflate or sulfonate catalysed by a palladium(0) complex." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Suzuki coupling reaction" EXACT [] synonym: "Suzuki cross-coupling" EXACT [] synonym: "Suzuki cross-coupling reaction" EXACT [] synonym: "Suzuki reaction" EXACT [] synonym: "Suzuki-Miyaura coupling" EXACT [] synonym: "Suzuki-Miyaura coupling reaction" EXACT [] synonym: "Suzuki-Miyaura cross-coupling" EXACT [] synonym: "Suzuki-Miyaura cross-coupling reaction" EXACT [] synonym: "Suzuki-Miyaura reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000424/ xref: NAMERXN:3.1 is_a: RXNO:0000592 ! Suzuki-type coupling relationship: RXNO:0000425 CHEBI:33364 ! has_catalyst platinum [Term] id: RXNO:0000141 name: Sharpless asymmetric epoxidation def: "The epoxidation of an allylic alcohol to give a beta,gamma-epoxy alcohol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is tert-butyl hydroperoxide, and the catalyst is a complex of titanium salt and optically active diethyl tartrate." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Katsuki-Sharpless asymmetric epoxidation" EXACT [] synonym: "Katsuki-Sharpless epoxidation" EXACT [] synonym: "Sharpless epoxidation" EXACT [] synonym: "Sharpless-Katsuki asymmetric epoxidation" EXACT [] synonym: "Sharpless-Katsuki epoxidation" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000397/ is_a: MOP:0000671 ! epoxidation is_a: RXNO:0000346 ! oxacycle synthesis relationship: RXNO:0000423 CHEBI:32955 ! has specified product epoxide relationship: RXNO:0000425 CHEBI:33341 ! has_catalyst titanium atom [Term] id: RXNO:0000142 name: Sharpless asymmetric dihydroxylation def: "The dihydroxylation of an alkene to give an alpha,beta-diol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is osmium tetroxide, which is used catalytically with a stoichiometric oxidant and a chiral ligand. The reagents are available commercially as AD-mix." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Sharpless bishydroxylation" EXACT [] synonym: "Sharpless hydroxylation" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000396/ is_a: RXNO:0000041 ! addition reaction step [Term] id: RXNO:0000143 name: Sharpless asymmetric aminohydroxylation def: "The aminohydroxylation of an alkene to give a beta-amino alcohol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is an oxygen-containing osmium species and/or an amino derivative which can be used catalytically with a stoichiometric oxidant and a chiral ligand." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Sharpless oxyamination" EXACT [] is_a: RXNO:0000041 ! addition reaction step [Term] id: RXNO:0000144 name: Kumada coupling def: "A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a palladium or nickel catalyst." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Kharasch cross-coupling" EXACT [] synonym: "Kumada cross-coupling" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000248/ is_a: RXNO:0000002 ! carbon-carbon coupling reaction union_of: RXNO:0000541 ! palladium-catalysed Kumada coupling union_of: RXNO:0000542 ! nickel-catalysed Kumada coupling [Term] id: RXNO:0000145 name: Barbier-Wieland degradation def: "The degradation of a carboxylic acid to its next lower homologous carboxylic acid." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Barbier-Wieland procedure" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000018/ is_a: RXNO:0000105 ! end-of-chain chain shortening [Term] id: RXNO:0000146 name: Corey-Fuchs reaction def: "A homologation reaction of an aldehyde to yield a terminal alkyne. The reagents are tetrabromomethane, triphenylphosphine, butyllithium and water." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Ramirez-Corey-Fuchs reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000089/ is_a: RXNO:0000070 ! chain lengthening relationship: has_part RXNO:0000250 ! Fritsch-Buttenberg-Wiechell rearrangement relationship: has_part RXNO:0000556 ! Corey-Fuchs terminal dibromoolefination relationship: RXNO:0000423 CHEBI:73477 ! has specified product terminal acetylenic compound relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde relationship: RXNO:0000424 CHEBI:47875 ! has specified reactant tetrabromomethane [Term] id: RXNO:0000147 name: Emde degradation def: "A reduction of a quaternary ammonium salt containing at least one unsaturated substituent, to give a tertiary amine." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Emde reaction" EXACT [] synonym: "Emde reduction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000127/ is_a: RXNO:0000073 ! cleaving reaction [Term] id: RXNO:0000148 name: Claisen rearrangement def: "The [3,3]-sigmatropic rearrangement of an allyl vinyl ether to give a gamma,delta-unsaturated carbonyl compound." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000080/ is_a: MOP:0000721 ! [3,3]-sigmatropic rearrangement is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000149 name: Ireland-Claisen rearrangement def: "The enolisation and subsequent [3,3]-sigmatropic rearrangement of an allylic acetate to give a gamma,delta-unsaturated carboxylic acid." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000080/ is_a: MOP:0000721 ! [3,3]-sigmatropic rearrangement is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000150 name: joining with rearrangement def: "A reaction in which one or more atoms are added to the molecular skeleton and a skeletal rearrangement occurs." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000000 ! molecular skeleton joining reaction intersection_of: RXNO:0000000 ! molecular skeleton joining reaction intersection_of: OBI:0000417 RXNO:0000488 ! achieves_planned_objective joining with rearrangement objective relationship: OBI:0000417 RXNO:0000488 ! achieves_planned_objective joining with rearrangement objective [Term] id: RXNO:0000151 name: Bellus-Claisen rearrangement def: "The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic ether or allylic thioether or allylic amine and a ketene to give the corresponding gamma,delta-unsaturated carbonyl compound." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: MOP:0000721 ! [3,3]-sigmatropic rearrangement is_a: RXNO:0000150 ! joining with rearrangement [Term] id: RXNO:0000152 name: Eschenmoser-Claisen rearrangement def: "The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic alcohol and alpha,alpha-dialkoxy ethylamine to give a gamma,delta-unsaturated dialkyl amide." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000080/ is_a: MOP:0000721 ! [3,3]-sigmatropic rearrangement is_a: RXNO:0000150 ! joining with rearrangement [Term] id: RXNO:0000153 name: Johnson-Claisen rearrangement def: "The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic alcohol and trimethyl orthoacetate to give a gamma,delta-unsaturated alkyl ester." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000080/ is_a: MOP:0000721 ! [3,3]-sigmatropic rearrangement is_a: RXNO:0000150 ! joining with rearrangement [Term] id: RXNO:0000154 name: Swern oxidation def: "The oxidation of a primary alcohol or secondary alcohol to an aldehyde or ketone respectively. Does not work with allylic or benzylic alcohols." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000426 is_a: MOP:0000572 ! alcohol oxidation is_a: RXNO:0000012 ! functional group oxidation [Term] id: RXNO:0000155 name: Finkelstein reaction def: "The conversion of an alkyl chloride, alkyl bromide or alkyl sulfonate ester to an alkyl iodide by SN2 substitution. The reaction relies upon the equilibrium being pushed to completion by the precipitation." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000141/ is_a: RXNO:0000011 ! functional group modification [Term] id: RXNO:0000156 name: Lossen rearrangement def: "The derivatisation (for example with tosyl chloride) and subsequent rearrangement of a hydroxamic acid to give an isocyanate." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000259/ is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000157 name: Nef reaction def: "The conversion of a primary nitroalkane or secondary nitroalkane to an aldehyde or ketone, respectively." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000297/ is_a: RXNO:0000011 ! functional group modification [Term] id: RXNO:0000158 name: Japp-Klingemann reaction def: "The reaction of a doubly activated methylene compound that has at least one carbonyl substituent with an aryl azide to give a hydrazone. Usually there is concomitant cleaving and oxidation of one of the carbonyl substituents." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000073 ! cleaving reaction [Term] id: RXNO:0000159 name: Doebner-Miller reaction def: "The formation of a quinoline from a primary aromatic amine and an alpha,beta-unsaturated carbonyl compound." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719] synonym: "Doebner-von Miller reaction" EXACT [] synonym: "Skraup-Doebner-von Miller quinoline synthesis" EXACT [] is_a: RXNO:0000052 ! fused-ring-system formation relationship: RXNO:0000424 CHEBI:33860 [Term] id: RXNO:0000160 name: Fmoc protection def: "The protection of an amine (often a peptide) as its 9H-fluoren-9-ylmethoxycarbonyl derivative." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719] is_a: RXNO:0000321 ! amino group protection relationship: RXNO:0000416 CHEBI:46882 ! protects amino group [Term] id: RXNO:0000161 name: Paal-Knorr synthesis def: "The cyclisation of a 1,4-dicarbonyl compound with another molecule to give a five-membered aromatic ring compound." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719] comment: Usually this gives rise to a heterocycle. is_a: RXNO:0000005 ! ring formation reaction step [Term] id: RXNO:0000162 name: Paal-Knorr furan synthesis def: "The cyclisation of a 1,4-dicarbonyl compound with an acid catalyst to give a furan." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000315/ is_a: RXNO:0000161 ! Paal-Knorr synthesis is_a: RXNO:0000346 ! oxacycle synthesis relationship: RXNO:0000423 CHEBI:24129 ! has specified product furans [Term] id: RXNO:0000163 name: Paal-Knorr thiophene synthesis def: "The cyclisation of a 1,4-dicarbonyl compound with phosphorus pentasulfide to give a thiophene." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719] is_a: RXNO:0000161 ! Paal-Knorr synthesis is_a: RXNO:0000348 ! thiacycle synthesis relationship: RXNO:0000423 CHEBI:26961 ! has specified product thiophenes [Term] id: RXNO:0000164 name: Paal-Knorr pyrrole synthesis def: "The cyclisation of a 1,4-dicarbonyl compound with an amine to give a pyrrole." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719] comment: Merck Index says "ammonia or primary amines" xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000316/ is_a: RXNO:0000161 ! Paal-Knorr synthesis is_a: RXNO:0000497 ! pyrrole synthesis relationship: RXNO:0000423 CHEBI:26455 ! has specified product pyrroles [Term] id: RXNO:0000165 name: Schotten-Baumann reaction def: "The coupling of an alcohol or amine with an acyl chloride to give an ester or amide. A two-phase solvent system is often used, to enable the acid generated during the reaction to be neutralised by the aqueous base, while the starting materials and products remain in the organic phase." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000392/ is_a: RXNO:0000331 ! substitution step [Term] id: RXNO:0000166 name: Hofmann elimination def: "The elimination of a methylated amine from an alkylamine to form an olefin. The reaction proceeds via the quaternary ammonium salt." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "exhaustive methylation" EXACT [] synonym: "Hofmann degradation" RELATED [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000205/ is_a: RXNO:0000123 ! molecular skeleton elimination reaction relationship: RXNO:0000423 CHEBI:33641 ! has specified product olefin relationship: RXNO:0000424 CHEBI:13759 ! has specified reactant alkylamine [Term] id: RXNO:0000167 name: Fischer-Speier esterification def: "The esterification of a carboxylic acid with an alcohol. Various Lewis acids or Bronsted acids may be used as catalyst." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Fischer esterification" EXACT [] is_a: RXNO:0000331 ! substitution step [Term] id: RXNO:0000168 name: Weerman reaction def: "The degradation of an alpha-hydroxy amide or an alpha,beta-unsaturated amide to the lower homologue aldehyde, especially in carbohydrate chemistry. The process proceeds via Hofmann degradation." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Weerman degradation" EXACT [] synonym: "Weerman's reaction" EXACT [] is_a: RXNO:0000105 ! end-of-chain chain shortening relationship: RXNO:0000423 CHEBI:17478 ! has specified product aldehyde [Term] id: RXNO:0000169 name: Dakin reaction def: "The reaction of ortho- or para-phenolic (or ortho- or para-anilinic) aldehydes or ketones with hydrogen peroxide to form bisphenols (or hydroxy anilines) and carboxylic acids." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000073 ! cleaving reaction relationship: RXNO:0000424 CHEBI:16240 ! has specified reactant hydrogen peroxide [Term] id: RXNO:0000170 name: Schmidt rearrangement, carboxylic acid def: "The reaction of a carboxylic acid with hydrazoic acid to give the lower homologue amine, with the loss of the terminal carbon atom." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000105 ! end-of-chain chain shortening [Term] id: RXNO:0000171 name: Schmidt rearrangement, ketone def: "The reaction of a ketone with hydrazoic acid with the insertion of an NH group between the carbonyl carbon and one of the R groups to form an amide." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000030 ! molecular skeleton insertion reaction [Term] id: RXNO:0000172 name: Schmidt rearrangement, tertiary alcohol def: "The reaction of a tertiary alcohol with hydrazoic acid with rearrangement to form an imide." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000030 ! molecular skeleton insertion reaction [Term] id: RXNO:0000173 name: Schmidt rearrangement, alkene def: "The reaction of an alkene with hydrazoic acid with rearrangement to form an imide." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000030 ! molecular skeleton insertion reaction [Term] id: RXNO:0000174 name: Sommelet-Hauser rearrangement def: "The [2,3]-sigmatropic rearrangement of a benzyl quaternary ammonium salt to form an aniline." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000175 name: Dakin-West reaction def: "The reaction of an amino acid with an acid anhydride to give an alpha-acylamido ketone. The reaction proceeds via the mixed anhydride and an oxazolone; the product is always racemic." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: RXNO:0000424 CHEBI:36606 [Term] id: RXNO:0000176 name: Beckmann fragmentation def: "The cleavage of an oxime to the corresponding nitrile and an alkyl halide. This reaction is related to the Beckmann rearrangement, and occurs when the R group that is anti to the oxime hydroxyl is quaternary." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000073 ! cleaving reaction [Term] id: RXNO:0000177 name: Kharasch reaction def: "The transfer of a hydrogen or halogen atom from a haloalkane to an alkene, giving the chain-extended halogenated alkane." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Kharasch addition reaction" EXACT [] is_a: RXNO:0000070 ! chain lengthening [Term] id: RXNO:0000178 name: Kharasch-Sosnovsky reaction def: "The allylic oxidation of an alkene with a peroxy ester or a peroxide to give the corresponding allylic alcohol derivative. The catalyst is a copper compound." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000331 ! substitution step [Term] id: RXNO:0000179 name: Elbs persulfate oxidation, phenol variant def: "The oxidation of a phenol to give a (predominantly para) diphenol using potassium persulfate." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000332 ! aromatic substitution step [Term] id: RXNO:0000180 name: Elbs persulfate oxidation, tolyl variant def: "The oxidation of a methyl-substituted aromatic compound to the corresponding benzaldehyde using potassium persulfate." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000012 ! functional group oxidation relationship: RXNO:0000423 CHEBI:22698 ! has specified product benzaldehydes [Term] id: RXNO:0000181 name: Boyland-Sims oxidation def: "The oxidation of an aromatic amine to give a (predominantly ortho) amino aryl sulfate using potassium persulfate followed by hydrolysis to yield the corresponding aminophenol." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000059/ is_a: RXNO:0000332 ! aromatic substitution step relationship: RXNO:0000424 CHEBI:33860 [Term] id: RXNO:0000182 name: Kolbe-Schmitt reaction def: "The (predominantly ortho) carboxylation of a phenoxide." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000239/ is_a: MOP:0000713 ! carboxylation is_a: RXNO:0000002 ! carbon-carbon coupling reaction relationship: BFO:0000078 CHEBI:16526 ! has participant ceasing to exist carbon dioxide [Term] id: RXNO:0000183 name: Perkow reaction def: "The reaction between an alpha-halocarbonyl compound and a trialkyl phosphite to give an enol phosphate." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] comment: not clear why this is where it is and not a sibling of the Arbuzov reaction (2014-02-17) xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000329/ is_a: RXNO:0000000 ! molecular skeleton joining reaction [Term] id: RXNO:0000184 name: Pfitzner-Moffatt oxidation def: "The oxidation of a primary or secondary alcohol to the corresponding aldehyde or ketone respectively using dimethyl sulfoxide, 1,3-dicyclohexylcarbodiimide and acid. The reaction proceeds via an alkoxysulfonium ylide." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Moffatt oxidation" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000335/ is_a: RXNO:0000012 ! functional group oxidation [Term] id: RXNO:0000185 name: Willgerodt reaction def: "The conversion of an aryl alkyl ketone to an amide and/or an ammonium salt of a carboxylic acid using ammonium polysulfide. The carbonyl group of the product is always at the end of the alkyl chain." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000011 ! functional group modification [Term] id: RXNO:0000186 name: Willgerodt-Kindler reaction def: "The conversion of an aryl alkyl ketone to an amide using sulfur and dry ammonia or a primary or secondary amine. The amide carbonyl group is always at the end of the alkyl chain." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000466/ is_a: RXNO:0000011 ! functional group modification [Term] id: RXNO:0000187 name: Tishchenko reaction def: "The formation of an ester from two aldehydes via a disproportionation process using a metal alkoxide to oxidise one aldehyde and reduce the other." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000433/ is_a: RXNO:0000011 ! functional group modification relationship: RXNO:0000423 CHEBI:33308 ! has specified product carboxylic ester relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde [Term] id: RXNO:0000188 name: Zimmermann reaction def: "The reaction between a methylene ketone and a polynitro aromatic compound." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000482/ is_a: RXNO:0000002 ! carbon-carbon coupling reaction [Term] id: RXNO:0000189 name: Neber rearrangement def: "The rearrangement of the sulfonic ester of a ketoxime in base to give an alpha-amino ketone." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000296/ is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000191 name: Nozaki-Hiyama-Kishi reaction def: "A coupling reaction of an aldehyde to an allyl, vinyl or aryl halide or triflate in the presence of chromium(II). It is catalysed by nickel." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Nozaki reaction" EXACT [] synonym: "Nozaki-Hiyama-Kishi coupling" EXACT [] synonym: "Nozaki-Kishi reaction" EXACT [] is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde [Term] id: RXNO:0000192 name: Buchwald-Hartwig amination def: "A reaction in which an aryl halide or aryl triflate reacts with a primary or secondary amine in the presence of base to give a secondary or tertiary amine. It is catalysed by a palladium catalyst." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Buchwald-Hartwig reaction" EXACT [] is_a: RXNO:0000332 ! aromatic substitution step relationship: RXNO:0000425 CHEBI:33363 ! has_catalyst palladium [Term] id: RXNO:0000193 name: Hiyama coupling def: "A carbon-carbon coupling reaction where an organosilane reacts with an organic halide or triflate. It is catalysed by a palladium or nickel complex." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Hiyama cross-coupling" EXACT [] is_a: RXNO:0000002 ! carbon-carbon coupling reaction [Term] id: RXNO:0000194 name: Stevens rearrangement def: "The 1,2-rearrangement of an alpha-methylene ammonium salt or alpha-methylene sulfonium salt to an amine or sulfide in the presence of strong base." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000195 name: Stevens rearrangement, ammonium def: "The 1,2-rearrangement of an alpha-methylene ammonium salt to an amine in the presence of strong base." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000194 ! Stevens rearrangement [Term] id: RXNO:0000196 name: Stevens rearrangement, sulfonium def: "The 1,2-rearrangement of an alpha-methylene sulfonium salt to a sulfide in the presence of strong base." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000194 ! Stevens rearrangement [Term] id: RXNO:0000197 name: aza-Cope rearrangement def: "A [3,3]-sigmatropic rearrangement where an aza-1,5-hexadiene rearranges to form an aza-1,5-hexadiene." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: MOP:0000721 ! [3,3]-sigmatropic rearrangement is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000198 name: 2-aza-Cope rearrangement def: "The rearrangement of a 2-aza-1,5-hexadiene to form an imine." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000197 ! aza-Cope rearrangement [Term] id: RXNO:0000199 name: 3-aza-Cope rearrangement def: "The rearrangement of a 3-aza-1,5-hexadiene to form a delta,epsilon-unsaturated imine." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] comment: This is the reverse of the 1-aza-Cope rearrangement. synonym: "amino-Claisen rearrangement" EXACT [] synonym: "aza-Claisen rearrangement" EXACT [] is_a: RXNO:0000197 ! aza-Cope rearrangement [Term] id: RXNO:0000200 name: 1-aza-Cope rearrangement def: "The rearrangement of a delta,epsilon-unsaturated imine to form a 3-aza-1,5-hexadiene." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] comment: This is the reverse of the 3-aza-Cope rearrangement. is_a: RXNO:0000197 ! aza-Cope rearrangement [Term] id: RXNO:0000201 name: Steglich rearrangement def: "The rearrangement of an oxazolyl carbonate to a C-carboxyazlactone." [http://orcid.org/0000-0001-5985-7429, RSC:jrw] is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000202 name: ring rearrangement def: "A reaction in which the number of rings in a molecule stays the same but the connectivity of the atoms in at least one ring changes." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000005 ! ring formation reaction step intersection_of: RXNO:0000005 ! ring formation reaction step intersection_of: OBI:0000417 RXNO:0000458 ! achieves_planned_objective molecular ring rearrangement objective relationship: OBI:0000417 RXNO:0000458 ! achieves_planned_objective molecular ring rearrangement objective [Term] id: RXNO:0000203 name: deprotection reaction def: "A reaction in which a protecting group is modified by converting it into a functional group." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:6 is_a: RXNO:0000010 ! functional modification intersection_of: RXNO:0000010 ! functional modification intersection_of: OBI:0000417 RXNO:0000484 ! achieves_planned_objective deprotection objective intersection_of: RXNO:0000417 CHEBI:24433 ! deprotects group relationship: OBI:0000417 RXNO:0000484 ! achieves_planned_objective deprotection objective relationship: part_of RXNO:0000329 ! planned synthesis relationship: RXNO:0000417 CHEBI:24433 ! deprotects group [Term] id: RXNO:0000204 name: multiple-bond metathesis def: "A joining reaction in which two carbon-carbon multiple bonds are redistributed among two fragments. The reaction is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene." [http://orcid.org/0000-0001-5985-7429] synonym: "metathesis" EXACT [] synonym: "multiple bond metathesis" EXACT [] is_a: RXNO:0000000 ! molecular skeleton joining reaction [Term] id: RXNO:0000205 name: ring breaking def: "A planned reaction step in which the product has fewer rings than the reactants." [http://orcid.org/0000-0001-5985-7429] synonym: "ring opening" EXACT [] synonym: "selective ring opening" EXACT [] is_a: RXNO:0000001 ! planned reaction step intersection_of: RXNO:0000001 ! planned reaction step intersection_of: OBI:0000417 RXNO:0000449 ! achieves_planned_objective molecular ring breaking objective relationship: OBI:0000417 RXNO:0000449 ! achieves_planned_objective molecular ring breaking objective [Term] id: RXNO:0000206 name: ring contraction def: "A planned reaction step in which an existing ring is reduced in size." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000005 ! ring formation reaction step relationship: OBI:0000417 RXNO:0000450 ! achieves_planned_objective molecular ring contraction objective [Term] id: RXNO:0000207 name: Strecker reaction def: "An addition reaction between a carbonyl compound, an inorganic cyanide and an ammonium salt, followed by hydrolysis, to give an alpha-amino carboxylic acid." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000070 ! chain lengthening [Term] id: RXNO:0000208 name: aromatic Claisen rearrangement def: "The [3,3]-sigmatropic rearrangement, and subsequent re-aromatisation, of an allyl aryl ether to give an ortho-allyl phenol." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: MOP:0000721 ! [3,3]-sigmatropic rearrangement is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000209 name: Nazarov cyclisation def: "The acid-catalysed cyclisation of a divinylketone to give a cyclopentenone." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Nazarov cyclization" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000295/ is_a: RXNO:0000005 ! ring formation reaction step relationship: has_part MOP:0000740 ! acid catalysis [Term] id: RXNO:0000210 name: Fleming-Tamao oxidation def: "The stereospecific oxidation of a (phenyldimethylsilyl)alkane to the corresponding alcohol using bromine, usually generated in situ from potassium bromide and peracetic acid." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Fleming oxidation" EXACT [] synonym: "Tamao-Fleming oxidation" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000150/ is_a: RXNO:0000331 ! substitution step [Term] id: RXNO:0000211 name: Tamao oxidation def: "The stereospecific oxidation of a (halosilyl)alkane to the corresponding alcohol using potassium fluoride and hydrogen peroxide." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Tamao-Kumada oxidation" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000150/ is_a: RXNO:0000331 ! substitution step relationship: OBI:0000417 RXNO:0000468 ! achieves_planned_objective molecular substitution objective relationship: RXNO:0000424 CHEBI:16240 ! has specified reactant hydrogen peroxide [Term] id: RXNO:0000212 name: Sakurai reaction, aldehyde or ketone def: "A carbon-carbon coupling reaction in which an aldehyde or ketone reacts with allyltrimethylsilane to form a homoallylic alcohol." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000000 ! molecular skeleton joining reaction is_a: RXNO:0000443 ! Sakurai reaction union_of: RXNO:0000451 ! aldehyde Sakurai reaction union_of: RXNO:0000452 ! ketone Sakurai reaction relationship: OBI:0000417 RXNO:0000440 ! achieves_planned_objective molecular skeleton joining objective [Term] id: RXNO:0000213 name: Sakurai reaction, enone def: "A carbon-carbon coupling reaction in which an enone reacts with allyltrimethylsilane to form a delta,epsilon-unsaturated carbonyl compound." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000443 ! Sakurai reaction [Term] id: RXNO:0000214 name: Sakurai reaction, acid chloride def: "A carbon-carbon coupling reaction in which an acid chloride reacts with allyltrimethylsilane to form a gamma,delta-unsaturated ketone." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000443 ! Sakurai reaction [Term] id: RXNO:0000215 name: Sakurai reaction, acetal or ketal def: "A carbon-carbon coupling reaction in which an acetal or ketal reacts with allyltrimethylsilane to form a homoallylic ether." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000443 ! Sakurai reaction [Term] id: RXNO:0000216 name: imine Sakurai reaction def: "A carbon-carbon coupling reaction in which an imine reacts with allyltrimethylsilane to form a homoallylic amine." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000443 ! Sakurai reaction [Term] id: RXNO:0000217 name: Sakurai reaction, epoxide def: "A ring-breaking reaction in which an epoxide reacts with allyltrimethylsilane to form a hydroxy alkene." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000205 ! ring breaking is_a: RXNO:0000443 ! Sakurai reaction [Term] id: RXNO:0000218 name: Cannizzaro reaction def: "The disproportionation of a non-enolisable aldehyde to the corresponding carboxylic acid and alcohol. The reaction is base-catalysed." [http://orcid.org/0000-0002-4077-4719, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000071/ is_a: RXNO:0000011 ! functional group modification relationship: RXNO:0000423 CHEBI:30879 ! has specified product alcohol relationship: RXNO:0000423 CHEBI:33575 ! has specified product carboxylic acid relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde [Term] id: RXNO:0000219 name: crossed Cannizzaro reaction def: "The reaction between two different non-enolisable aldehydes to give a carboxylic acid and an alcohol. The reaction is base-catalysed." [http://orcid.org/0000-0002-4077-4719, http://orcid.org/0000-0002-4077-4719, RSC:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000071/ is_a: RXNO:0000011 ! functional group modification relationship: RXNO:0000423 CHEBI:30879 ! has specified product alcohol relationship: RXNO:0000423 CHEBI:33575 ! has specified product carboxylic acid relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde [Term] id: RXNO:0000220 name: Pummerer rearrangement def: "The conversion of a sulfoxide with an alpha-hydrogen to an alpha-substituted thioether. The reaction is usually performed with an acid anhydride or acyl halide." [http://orcid.org/0000-0002-4077-4719, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Pummerer methyl sulfoxide rearrangement" EXACT [] is_a: RXNO:0000011 ! functional group modification [Term] id: RXNO:0000221 name: Polonovski reaction def: "The reaction of a tertiary amine oxide with an anhydride or acyl chloride to give an N,N-disubstituted acetamide and an aldehyde." [http://orcid.org/0000-0002-4077-4719, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000073 ! cleaving reaction relationship: RXNO:0000423 CHEBI:17478 ! has specified product aldehyde [Term] id: RXNO:0000222 name: Polonovski-Potier reaction def: "The reaction of a tertiary amine oxide with trifluoroacetic anhydride to give an N,N-disubstituted acetamide and an aldehyde." [http://orcid.org/0000-0002-4077-4719, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Potier-Polonovski reaction" EXACT [] is_a: RXNO:0000221 ! Polonovski reaction relationship: RXNO:0000423 CHEBI:17478 ! has specified product aldehyde [Term] id: RXNO:0000223 name: Menshutkin reaction alt_id: RXNO:0000375 def: "The alkylation of a tertiary amine with an alkyl halide to the corresponding ammonium salt." [http://orcid.org/0000-0002-4077-4719, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Menschutkin reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000275/ is_a: MOP:0002369 ! N-alkylation is_a: RXNO:0000012 ! functional group oxidation relationship: RXNO:0000424 CHEBI:32876 [Term] id: RXNO:0000224 name: Strecker degradation def: "The deamination and decarboxylation of amino acids to imines and then to aldehydes or ketones, in the presence of a carbonyl compound (especially an alpha,beta-dicarbonyl compound or a reducing sugar such as glucose). The reaction is involved in the generation of meat aromas/flavours in cooking." [http://orcid.org/0000-0002-4077-4719, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000105 ! end-of-chain chain shortening [Term] id: RXNO:0000225 name: Wohl-Ziegler bromination def: "The allylic or benzylic bromination of hydrocarbons using an N-bromoimide and a radical initiator, to give an allylic or benzylic bromide." [http://orcid.org/0000-0002-4077-4719, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Wohl-Ziegler reaction" EXACT [] is_a: RXNO:0000373 ! functional group addition step [Term] id: RXNO:0000226 name: Wolff-Kishner reduction def: "The reduction of an aldehyde or ketone to the corresponding methylene compound, using hydrazine hydrate and a base." [http://orcid.org/0000-0002-4077-4719, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000037 ! functional group reduction [Term] id: RXNO:0000227 name: Wolff-Kishner reduction, Huang-Minlon modification def: "The reduction of an aldehyde or ketone to the corresponding methylene compound, using hydrazine hydrate and a base in refluxing ethylene glycol." [http://orcid.org/0000-0002-4077-4719, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Huang-Minlon modification" EXACT [] is_a: RXNO:0000226 ! Wolff-Kishner reduction [Term] id: RXNO:0000228 name: Zemplen transesterification def: "The reduction of an ester to the corresponding alcohol, using sodium methoxide in dry methanol." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] synonym: "Zemplen procedure" EXACT [] is_a: RXNO:0000037 ! functional group reduction [Term] id: RXNO:0000229 name: Ferrier rearrangement def: "The rearrangement of an O-alkenyl acetal to give the corresponding beta-alkoxy carbonyl compound." [http://orcid.org/0000-0002-4077-4719] synonym: "Ferrier reaction" EXACT [] is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000230 name: aza-Ferrier rearrangement def: "The rearrangement of an O-alkenyl hemiaminal ether to give the corresponding beta-amino carbonyl compound." [http://orcid.org/0000-0002-4077-4719] synonym: "aza-Ferrier reaction" EXACT [] is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000231 name: aza-ene reaction def: "A joining reaction where an N=C system with an allylic hydrogen reacts with a compound containing a multiple bond (an enophile) to form a substituted alkene." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000000 ! molecular skeleton joining reaction [Term] id: RXNO:0000232 name: Petasis reaction def: "The alkylation of an amine with a boronic acid and an aldehyde to give a substituted amine." [RSC:db] synonym: "Petasis three-component coupling" EXACT [] is_a: RXNO:0000011 ! functional group modification relationship: RXNO:0000423 CHEBI:32952 ! has specified product amine relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde relationship: RXNO:0000424 CHEBI:32952 ! has specified reactant amine relationship: RXNO:0000424 CHEBI:38269 ! has specified reactant boronic acids [Term] id: RXNO:0000233 name: Achmatowicz rearrangement def: "A rearrangement of a furfuryl alcohol derivative to a dihydropyranone, from which monosaccharides may be synthesised." [RSC:db] is_a: RXNO:0000202 ! ring rearrangement [Term] id: RXNO:0000234 name: aza-Achmatowicz rearrangement def: "A rearrangement of a furfuryl amine derivative to a tetrahydropyridinone." [RSC:db] is_a: RXNO:0000202 ! ring rearrangement [Term] id: RXNO:0000235 name: aza-Henry reaction def: "A carbon-carbon coupling reaction between a nitroalkane and an imine to give a beta-amino nitroalkane." [RSC:db] is_a: RXNO:0000002 ! carbon-carbon coupling reaction [Term] id: RXNO:0000236 name: Biginelli reaction def: "A three-component coupling of a beta-keto ester, an aldehyde and urea to give a 3,4-dihydropyrimidinone." [RSC:db] synonym: "Biginelli condensation" EXACT [] synonym: "Biginelli pyrimidone synthesis" EXACT [] synonym: "Biginelli three-component reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000043/ is_a: MOP:0000628 ! molecular dehydration reaction is_a: RXNO:0000005 ! ring formation reaction step relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde [Term] id: RXNO:0000237 name: Blaise reaction def: "The coupling of an alpha-bromo ester with a nitrile to give a beta-ketoester, in the presence of zinc." [RSC:db] is_a: RXNO:0000002 ! carbon-carbon coupling reaction relationship: RXNO:0000425 CHEBI:27363 [Term] id: RXNO:0000238 name: Katritzky pyrylium-pyridinium method def: "The substitution of an amine with a nucleophile using a pyrylium salt." [http://orcid.org/0000-0002-4077-4719] is_a: RXNO:0000331 ! substitution step [Term] id: RXNO:0000239 name: metalla-aza-Claisen rearrangement def: "The rearrangement of a 3-aza-4-metalla-1,5-hexadiene to form a delta,epsilon-unsaturated metallaimine." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719] is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000240 name: Bergman cyclisation def: "The cyclisation of an ene-diyne to give a 1,4-diradical cyclohexatriene. The diradical usually aromatises." [http://orcid.org/0000-0002-4077-4719] synonym: "Bergman cyclization" EXACT [] synonym: "Bergman reaction" EXACT [] synonym: "Masamune-Bergman cyclisation" EXACT [] synonym: "Masamune-Bergman cyclization" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000037/ is_a: RXNO:0000005 ! ring formation reaction step [Term] id: RXNO:0000241 name: nitro-Michael reaction def: "A conjugate addition reaction where a carbon nucleophile adds to an alpha,beta-unsaturated nitro compound." [http://orcid.org/0000-0002-4077-4719] is_a: RXNO:0000009 ! Michael addition [Term] id: RXNO:0000242 name: Noyori asymmetric hydrogenation, alkene def: "The homogeneous asymmetric catalytic hydrogenation of a C=C double bond using a ruthenium(II) BINAP catalyst." [http://orcid.org/0000-0002-4077-4719] synonym: "Noyori hydrogenation, alkene" EXACT [] is_a: RXNO:0000041 ! addition reaction step [Term] id: RXNO:0000243 name: Noyori asymmetric hydrogenation, carbonyl def: "The homogeneous asymmetric catalytic hydrogenation of a carbonyl bond using a ruthenium(II) BINAP catalyst." [http://orcid.org/0000-0002-4077-4719] synonym: "Noyori hydrogenation, carbonyl" EXACT [] is_a: RXNO:0000037 ! functional group reduction [Term] id: RXNO:0000244 name: Passerini reaction def: "The reaction between an isonitrile, a carboxylic acid and aldehyde or ketone to give an alpha-acyloxy amide." [http://orcid.org/0000-0002-4077-4719] is_a: RXNO:0000000 ! molecular skeleton joining reaction [Term] id: RXNO:0000245 name: ring-closing metathesis def: "A joining reaction in which two carbon-carbon double bonds in the same molecule are redistributed to give a cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene." [http://orcid.org/0000-0002-4077-4719] synonym: "RCM" EXACT [] synonym: "ring closing alkene metathesis" EXACT [] synonym: "ring closing metathesis" EXACT [] synonym: "ring closing olefin metathesis" EXACT [] synonym: "ring-closing alkene metathesis" EXACT [] synonym: "ring-closing olefin metathesis" EXACT [] is_a: RXNO:0000005 ! ring formation reaction step [Term] id: RXNO:0000246 name: polymerisation reaction def: "A joining reaction, the objective of which is that a large number of monomers react together to produce a polymer consisting of repeating units." [rsc:db] synonym: "polymerisation" EXACT [] synonym: "polymerization" EXACT [] synonym: "polymerization reaction" EXACT [] is_a: RXNO:0000000 ! molecular skeleton joining reaction intersection_of: RXNO:0000000 ! molecular skeleton joining reaction intersection_of: OBI:0000417 RXNO:0000466 ! achieves_planned_objective polymerisation objective intersection_of: RXNO:0000423 CHEBI:33839 ! has specified product macromolecule relationship: OBI:0000417 RXNO:0000466 ! achieves_planned_objective polymerisation objective relationship: RXNO:0000423 CHEBI:33839 ! has specified product macromolecule [Term] id: RXNO:0000247 name: ring-opening metathesis polymerisation def: "A joining reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. two alkenes. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of ring strain in the cycloalkene." [http://orcid.org/0000-0002-4077-4719, rsc:db] synonym: "ring-opening metathesis polymerization" EXACT [] synonym: "ROMP" EXACT [] is_a: RXNO:0000246 ! polymerisation reaction [Term] id: RXNO:0000248 name: Carroll rearrangement def: "An adaptation of the Claisen rearrangement that transforms a beta-keto allyl ester into a gamma,delta-allyl ketone. It uses base and high temperature or milder conditions with a ruthenium or palladium complex as catalyst." [RSC:db] synonym: "Kimel-Cope rearrangement" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000072/ is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000249 name: Bose-Mitsunobu reaction def: "A Mitsunobu reaction, where an alcohol is converted to something else with inversion at the stereocentre, using diphenylphosphoryl azide." [RSC:db] is_a: RXNO:0000034 ! Mitsunobu reaction [Term] id: RXNO:0000250 name: Fritsch-Buttenberg-Wiechell rearrangement def: "The rearrangement of a 2-bromoalkene into an alkyne, mediated by strong base." [RSC:db] is_a: RXNO:0000025 ! rearrangement step relationship: RXNO:0000423 CHEBI:73474 xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000161/ [Term] id: RXNO:0000251 name: Stork-Wittig olefination def: "A carbon-carbon coupling reaction where an aldehyde reacts with a phosphonium salt to give a Z-iodoalkene. The reaction is mediated by sodium or potassium hexamethyldisilazide." [RSC:db] is_a: RXNO:0000479 ! olefination relationship: RXNO:0000423 CHEBI:33641 ! has specified product olefin relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde [Term] id: RXNO:0000252 name: Cadogan carbazole synthesis def: "The reduction of a 2-nitrobiaryl compound to give a carbazole." [doi:10.1039/JR9650004831, http://orcid.org/0000-0002-4077-4719] is_a: RXNO:0000521 ! carbazole synthesis relationship: RXNO:0000423 CHEBI:48513 ! has specified product carbazoles [Term] id: RXNO:0000253 name: Cadogan coupling def: "The arylation of an arylamine mediated by isopentyl nitrite." [doi:10.1039/b409373a, http://orcid.org/0000-0002-4077-4719] is_a: RXNO:0000002 ! carbon-carbon coupling reaction [Term] id: RXNO:0000254 name: MacDonald condensation def: "The reaction between a 1,9-diformyldipyrromethane and a dipyrromethane to give a porphodimethene." [doi:10.1039/a908784b, http://orcid.org/0000-0002-4077-4719] is_a: RXNO:0000052 ! fused-ring-system formation [Term] id: RXNO:0000255 name: Zweifel diene synthesis def: "The carbon-carbon homocoupling reaction of a pair of alkyne molecules using a borane and iodine. The reaction proceeds via a borane intermediate." [isbn:9780521096430, http://orcid.org/0000-0002-4077-4719] is_a: RXNO:0000039 ! carbon-carbon homocoupling reaction [Term] id: RXNO:0000256 name: Dess-Martin oxidation def: "The oxidation of a primary alcohol to an aldehyde or a secondary alcohol to a ketone using the Dess-Martin periodinane." [http://orcid.org/0000-0001-5985-7429] synonym: "Dess-Martin periodinane oxidation" EXACT [] is_a: MOP:0000572 ! alcohol oxidation is_a: RXNO:0000012 ! functional group oxidation [Term] id: RXNO:0000257 name: Criegee oxidation def: "The oxidative cleavage of an alpha,beta-diol using lead tetraacetate to give the corresponding carbonyl compounds." [http://orcid.org/0000-0001-5985-7429] synonym: "Criegee glycol cleavage" EXACT [] synonym: "Criegee reaction" EXACT [] is_a: RXNO:0000073 ! cleaving reaction is_a: RXNO:0000344 ! alkene oxidative cleavage [Term] id: RXNO:0000258 name: Simmons-Smith reaction def: "A ring formation reaction where an alkene reacts with a dihalomethane in the presence of a metal atom or metal complexes to form a cyclopropane. The traditional reaction uses a zinc-copper couple and diiodomethane." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000005 ! ring formation reaction step relationship: RXNO:0000423 CHEBI:51454 relationship: RXNO:0000424 CHEBI:33641 xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000400/ [Term] id: CHEBI:51454 name: cyclopropanes is_a: CHEBI:33595 [Term] id: RXNO:0000259 name: Wittig rearrangement def: "Any of a family of sigmatropic rearrangements that involve the migration of a group on an electronegative atom (O or N) to a carbon atom." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, rsc:db] is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000260 name: [1,2]-Wittig rearrangement def: "A base-mediated 1,2-sigmatropic rearrangement of an ether to give an alcohol." [rsc:db] synonym: "1,2-Wittig rearrangement" EXACT [] synonym: "[1,2] Wittig rearrangement" EXACT [] is_a: RXNO:0000259 ! Wittig rearrangement relationship: RXNO:0000423 CHEBI:30879 relationship: RXNO:0000424 CHEBI:25698 [Term] id: CHEBI:25698 name: ether is_a: CHEBI:36963 [Term] id: CHEBI:36963 name: organooxygen compound is_a: CHEBI:23367 [Term] id: RXNO:0000261 name: [2,3]-Wittig rearrangement def: "A base-mediated 2,3-sigmatropic rearrangement of an allyl ether to give a homoallylic alcohol." [rsc:db] synonym: "2,3-Wittig rearrangement" EXACT [] synonym: "[2,3] Wittig rearrangement" EXACT [] is_a: RXNO:0000259 ! Wittig rearrangement [Term] id: RXNO:0000262 name: [1,2]-aza-Wittig rearrangement def: "A base-mediated 1,2-sigmatropic rearrangement of a tertiary amine to give a secondary amine." [rsc:db] synonym: "1,2-aza-Wittig rearrangement" EXACT [] synonym: "[1,2] aza-Wittig rearrangement" EXACT [] is_a: RXNO:0000259 ! Wittig rearrangement relationship: RXNO:0000423 CHEBI:32863 relationship: RXNO:0000424 CHEBI:32876 [Term] id: RXNO:0000263 name: [2,3]-aza-Wittig rearrangement def: "A base-mediated 2,3-sigmatropic rearrangement of an activated tertiary allyl amine, to give a secondary homoallylic amine." [rsc:db] synonym: "2,3-aza-Wittig rearrangement" EXACT [] synonym: "[2,3] aza-Wittig rearrangement" EXACT [] is_a: RXNO:0000259 ! Wittig rearrangement [Term] id: RXNO:0000264 name: aza-Baylis-Hillman reaction def: "A carbon-carbon coupling of an imine to an activated alkene in the presence of a nucleophilic base to give an allylic amine." [rsc:db] synonym: "aza-Morita-Baylis-Hillman reaction" EXACT [] is_a: RXNO:0000076 ! Baylis-Hillman reaction [Term] id: RXNO:0000265 name: aza-Wittig reaction def: "Reaction of a carbonyl compound with a phosphazene to give an imine." [rsc:db] is_a: RXNO:0000367 ! carbonyl compound to imine conversion [Term] id: RXNO:0000266 name: Fenton reaction alt_id: RXNO:0000267 def: "Either: (a) The oxidation of a 1,2-glycol with Fenton's reagent (hydrogen peroxide and iron salts) to give an alpha-hydroxy aldehyde; (b) The oxidation of an alpha-hydroxy carboxylic acid with Fenton's reagent to give an alpha-keto carboxylic acid; or (c) the reaction of the components of Fenton's reagent, viz. reduction of hydrogen peroxide by Fe(II) , producing an hydroxyl radical." [rsc:db] synonym: "Fenton's reaction" EXACT [] is_a: RXNO:0000012 ! functional group oxidation [Term] id: RXNO:0000268 name: Hantzsch pyridine synthesis def: "A ring-forming reaction between two equivalents of a beta-ketoester, an aldehyde and ammonia (or an ammonium salt), to give a dihydropyridine. The dihydropyridine can be oxidised to a pyridine using an oxidising agent." [rsc:db] synonym: "Hantzsch dihydropyridine synthesis" EXACT [] is_a: RXNO:0000520 ! pyridine synthesis relationship: RXNO:0000423 CHEBI:50075 ! has specified product dihydropyridine relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde [Term] id: RXNO:0000269 name: alkyne-azide click reaction def: "A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole, needing only heat to proceed." [rsc:db] comment: Note: The term "click reaction" was originally used in a broader sense to refer to any coupling that took place cleanly and quickly in quantitative yield, but it now always seems to be used in this narrower sense. synonym: "\"click\" reaction" EXACT [] synonym: "'click' reaction" EXACT [] synonym: "alkyne-azide Huisgen cycloaddition" EXACT [] synonym: "alkyne-azide Huisgen reaction" EXACT [] synonym: "azide-alkyne click reaction" EXACT [] synonym: "azide-alkyne Huisgen cycloaddition" EXACT [] synonym: "azide-alkyne Huisgen reaction" EXACT [] synonym: "click reaction" EXACT [] synonym: "Huisgen cycloaddition" BROAD [] synonym: "Huisgen reaction" BROAD [] synonym: "Huisgen's 1,3-dipolar cycloaddition" BROAD [] is_a: MOP:0000715 ! [3+2] cycloaddition is_a: RXNO:0000018 ! 1,3-dipolar cycloaddition relationship: RXNO:0000424 CHEBI:22680 relationship: RXNO:0000424 CHEBI:73474 relationship: RXNO:0000423 CHEBI:35562 [Term] id: RXNO:0000270 name: copper(I)-catalyzed azide-alkyne cycloaddition def: "A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole as a single regioisomer." [RSC:db] comment: Commonly described as a variant of the (uncatalyzed) alkyne-azide click reaction, the mechanism of reaction is different, and thus formally it is not a 1,3-dipolar cycloaddition. [rsc:db] synonym: "copper(I)-catalysed alkyne-azide cycloaddition" EXACT [] synonym: "copper(I)-catalysed azide-alkyne click reaction" EXACT [] synonym: "copper(I)-catalysed azide-alkyne cycloaddition" EXACT [] synonym: "copper(I)-catalyzed alkyne-azide cycloaddition" EXACT [] synonym: "copper(I)-catalyzed azide-alkyne click reaction" EXACT [] synonym: "copper(I)-catalyzed azide-alkyne cycloaddition" EXACT [] synonym: "CuAAC" EXACT [] is_a: MOP:0000715 ! [3+2] cycloaddition relationship: RXNO:0000424 CHEBI:22680 relationship: RXNO:0000424 CHEBI:73474 relationship: RXNO:0000423 CHEBI:35562 [Term] id: CHEBI:35562 name: 1,2,3-triazole is_a: CHEBI:38597 [Term] id: CHEBI:38597 name: triazole is_a: CHEBI:35352 [Term] id: CHEBI:35352 name: organonitrogen compound is_a: CHEBI:23367 [Term] id: RXNO:0000271 name: Fischer-Tropsch process def: "A process in which carbon monoxide and hydrogen ('syngas') are converted into various liquid hydrocarbons." [rsc:db] synonym: "Fischer-Tropsch reaction" EXACT [] synonym: "Fischer-Tropsch synthesis" EXACT [] is_a: RXNO:0000000 ! molecular skeleton joining reaction [Term] id: RXNO:0000272 name: hydroformylation def: "The reaction of hydrogen and carbon monoxide with an alkene, to give an aldehyde, catalysed by a rhodium or cobalt catalyst. The process is equivalent to the formal addition of the H-C bond of formaldehyde across the double bond of an alkene." [rsc:db] is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: RXNO:0000423 CHEBI:17478 ! has specified product aldehyde [Term] id: RXNO:0000273 name: retro-Diels-Alder reaction def: "The reverse of a [4+2] cycloaddition reaction, in which an unsaturated six-membered ring compound fragments to give a diene and a compound containing a double or triple bond (a dienophile)." [rsc:db] synonym: "retro Diels-Alder reaction" EXACT [] is_a: RXNO:0000205 ! ring breaking relationship: RXNO:0000424 CHEBI:37613 [Term] id: CHEBI:37613 name: cyclohexadiene is_a: CHEBI:33641 is_a: CHEBI:33595 [Term] id: RXNO:0000274 name: retro-aldol addition def: "The reverse of an aldol addition, in which a beta-hydroxy ketone fragments to form a carbonyl compound and the enolate of an alpha-acidic carbonyl compound." [rsc:db] comment: This process can occur because the whole reaction is an equilibrium. In the forward direction (aldol addition), elimination of water from the beta-hydroxy ketone, giving an alpha,beta-unsaturated ketone, is irreversible, and thus the aldol condensation does not have a "retro" counterpart. synonym: "retro-aldol reaction" EXACT [] is_a: RXNO:0000073 ! cleaving reaction [Term] id: RXNO:0000275 name: Stork-Crabtree hydrogenation def: "A hydrogenation in which a metal-ligating group distant from the reacting alkene directs the attack of hydrogen, giving preferentially one stereoisomer of the product." [doi:10.1021/jo00364a007, rsc:db] is_a: RXNO:0000041 ! addition reaction step [Term] id: RXNO:0000276 name: Aufbau reaction def: "The insertion of alkenes (usually ethene) into the Al-C bond of an aluminium alkyl, to give a long-chain aluminium alkyl that can go on to react again, or can decompose into the corresponding terminal alkene. The addition of transition metals results in reliable production of high molecular weight polymers." [rsc:db] synonym: "\"Aufbau\" reaction" EXACT [] synonym: "'Aufbau' reaction" EXACT [] synonym: "Aufbau process" EXACT [] is_a: RXNO:0000246 ! polymerisation reaction [Term] id: RXNO:0000277 name: hydroalumination def: "The reaction of an aluminium alkyl with an alkene, to give an intermediate aluminium species that can give various products after work-up." [rsc:db] is_a: RXNO:0000294 ! hydrometallation [Term] id: RXNO:0000278 name: hydrovinylation def: "The reaction of two alkenes to give an elongated alkene, employing a transition-metal-based catalyst." [rsc:db] synonym: "1,2-hydrovinylation" EXACT [] is_a: RXNO:0000002 ! carbon-carbon coupling reaction [Term] id: RXNO:0000279 name: 1,4-hydrovinylation def: "The reaction of a 1,3-diene with an alkene to give a 1,4-diene, usually employing a cobalt-based catalyst (see Hilt and Luers, Synthesis, 2002, 609)." [rsc:db] is_a: RXNO:0000278 ! hydrovinylation [Term] id: RXNO:0000280 name: alkene metathesis def: "A joining reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. two alkenes. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene." [rsc:db] synonym: "cross metathesis" EXACT [] synonym: "cross-metathesis" EXACT [] synonym: "Grubbs metathesis" EXACT [] synonym: "Grubbs reaction" EXACT [] synonym: "olefin metathesis" EXACT [] synonym: "transalkylidenation" EXACT [] is_a: RXNO:0000204 ! multiple-bond metathesis [Term] id: RXNO:0000281 name: alkyne metathesis def: "A joining reaction in which two carbon-carbon triple bonds are redistributed among two fragments, i.e. two alkynes. It is catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutenes). The reaction is driven by release of a low-MW alkyne." [rsc:db] is_a: RXNO:0000204 ! multiple-bond metathesis [Term] id: RXNO:0000282 name: enyne metathesis def: "A joining reaction in which a carbon-carbon double bond and a carbon-carbon triple bond are redistributed among two fragments, i.e. an alkene and an alkyne. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutenes). As a low-MW alkene is not released, the reaction is usually driven by formation of a ring." [rsc:db] is_a: RXNO:0000204 ! multiple-bond metathesis [Term] id: RXNO:0000283 name: ring-closing enyne metathesis def: "A joining reaction in which a carbon-carbon double bond and a carbon-carbon triple bond in the same molecule are redistributed to give a alkene-substituted cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by formation of the ring." [rsc:db] synonym: "ring closing enyne metathesis" EXACT [] is_a: RXNO:0000005 ! ring formation reaction step [Term] id: RXNO:0000284 name: ring-opening metathesis def: "A ring-breaking reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. an alkene and a cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of ring strain in the cycloalkene." [rsc:db] synonym: "ring opening metathesis" EXACT [] is_a: RXNO:0000205 ! ring breaking [Term] id: RXNO:0000285 name: Luche reaction def: "A carbon-carbon coupling reaction where an aldehyde or ketone reacts with an allyl halide and zinc to give a homoallylic alcohol." [http://orcid.org/0000-0002-4077-4719, rsc:db] comment: Not to be confused with the Luche reduction (the chemoselective reduction of an enone to an allylic alcohol). is_a: RXNO:0000002 ! carbon-carbon coupling reaction relationship: RXNO:0000425 CHEBI:27363 [Term] id: CHEBI:27363 name: zinc atom is_a: CHEBI:27081 ! transition element atom [Term] id: CHEBI:27081 name: transition element atom is_a: CHEBI:33521 ! metal atom [Term] id: CHEBI:33521 name: metal atom is_a: CHEBI:33250 [Term] id: CHEBI:33250 name: atom is_a: CHEBI:24431 [Term] id: RXNO:0000286 name: Luche reduction def: "The chemoselective reduction of an enone to give an allylic alcohol, using sodium borohydride and an lanthanoid chloride, typically cerium chloride." [http://orcid.org/0000-0002-4077-4719, rsc:db] comment: Not to be confused with the Luche reaction (the coupling of an aldehyde or ketone with an allyl halide). is_a: RXNO:0000037 ! functional group reduction [Term] id: RXNO:0000287 name: Lindgren oxidation def: "The oxidation of an aldehyde to a carboxylic acid with chlorite." [doi:10.3891/acta.chem.scand.27-0888, http://orcid.org/0000-0002-4077-4719, rsc:db] is_a: RXNO:0000012 ! functional group oxidation relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde [Term] id: RXNO:0000288 name: Rosenmund-von Braun reaction def: "A carbon-carbon coupling reaction where an aryl halide reacts with copper(I) cyanide to give an aryl nitrile." [http://orcid.org/0000-0002-4077-4719, rsc:db] synonym: "Rosenmund-von Braun synthesis" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000376/ is_a: RXNO:0000002 ! carbon-carbon coupling reaction [Term] id: RXNO:0000289 name: Woehler reaction def: "The formation of urea from ammonium cyanate. Ammonium cyanate is unstable, and so is formed in situ from either (a) cyanic acid and ammonia, (b) a metal cyanate and an ammonium salt, or (c) a metal cyanate and ammonia." [http://orcid.org/0000-0002-4077-4719, rsc:db] synonym: "Woehler synthesis" EXACT [] synonym: "Wohler reaction" EXACT [] synonym: "Wohler synthesis" EXACT [] is_a: RXNO:0000011 ! functional group modification [Term] id: RXNO:0000290 name: hydrosilylation def: "The addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane. Addition to an aldehyde or ketone produces a silyl ether." [http://orcid.org/0000-0002-4077-4719, rsc:db] synonym: "hydrosilation" EXACT [] is_a: RXNO:0000041 ! addition reaction step [Term] id: RXNO:0000291 name: hydroamination def: "The addition of the N-H bond of an amine across a double bond of an alkene or alkyne, to give a more substituted amine." [http://orcid.org/0000-0002-4077-4719, rsc:db] is_a: RXNO:0000041 ! addition reaction step [Term] id: RXNO:0000292 name: hydroboration def: "The addition of a boron hydride across a double bond of an alkene or alkyne. The boron usually adds to the less substituted carbon." [http://orcid.org/0000-0002-4077-4719, rsc:db] is_a: RXNO:0000041 ! addition reaction step [Term] id: RXNO:0000293 name: hydroboration-oxidation def: "The formal addition of water across a double bond of an alkene or alkyne by formation of an organoborane and in situ oxidation, typically with basic peroxide. The product is usually the less substituted alcohol." [http://orcid.org/0000-0002-4077-4719, rsc:db] is_a: RXNO:0000041 ! addition reaction step [Term] id: RXNO:0000294 name: hydrometallation def: "The reaction of any of a number of metal hydride species with an alkene or alkyne, to give an intermediate organometal species that can give various products after work-up." [http://orcid.org/0000-0002-4077-4719, rsc:db] synonym: "hydrometalation" EXACT [] is_a: RXNO:0000041 ! addition reaction step [Term] id: RXNO:0000295 name: hydrozirconation def: "The reaction of a organozirconium hydride with an alkene or alkyne, to give an intermediate zirconium species that can give various products after work-up. The zirconium reagent used is typically Schwartz's reagent, Cp2ZrHCl." [http://orcid.org/0000-0002-4077-4719, rsc:db] is_a: RXNO:0000294 ! hydrometallation [Term] id: RXNO:0000296 name: hydrostannylation def: "The reaction of a organotin hydride with an alkene or alkyne, to give an intermediate tin species that can give various products after work-up." [http://orcid.org/0000-0002-4077-4719, rsc:db] is_a: RXNO:0000294 ! hydrometallation [Term] id: RXNO:0000297 name: hydrotelluration def: "The reaction of a organotellurium hydride with an alkyne, to give a (usually (Z)-configured) vinyltellurium species." [http://orcid.org/0000-0002-4077-4719, rsc:db] is_a: RXNO:0000294 ! hydrometallation [Term] id: RXNO:0000298 name: Fetizon oxidation def: "The oxidation of a primary alcohol to an aldehyde or a secondary alcohol to a ketone using Fetizon's reagent." [\:cg, rsc:db] is_a: RXNO:0000012 ! functional group oxidation [Term] id: RXNO:0000299 name: Vorbrueggen condensation def: "The substitution of an acylated sugar with a silylated base to give a nucleoside." [\:, http://orcid.org/0000-0002-4077-4719, rsc:db] synonym: "Vorbrueggen glycosylation" EXACT [] synonym: "Vorbruggen condensation" EXACT [] synonym: "Vorbruggen glycosylation" EXACT [] is_a: RXNO:0000000 ! molecular skeleton joining reaction [Term] id: RXNO:0000300 name: thiol-ene reaction def: "The addition of a thiol across the double bond of an alkene to give a thioether." [\:cg, rsc:db] synonym: "thiol-ene click reaction" EXACT [] is_a: RXNO:0000000 ! molecular skeleton joining reaction [Term] id: RXNO:0000301 name: Yamamoto polymerisation def: "The nickel-catalysed carbon-carbon coupling of a dihaloaromatic compound or aromatic bistriflate to give a polymer." [http://orcid.org/0000-0002-4077-4719, rsc:db] synonym: "Yamamoto coupling" EXACT [] synonym: "Yamamoto polymerization" EXACT [] is_a: RXNO:0000246 ! polymerisation reaction [Term] id: RXNO:0000302 name: thermal hydrosilylation def: "The thermally induced addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane, usually applied to cases where the hydrosilane is part of a silicon surface." [\:cg, rsc:db] is_a: RXNO:0000290 ! hydrosilylation [Term] id: RXNO:0000303 name: photohydrosilylation def: "The photochemically induced addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane, usually applied to cases where the hydrosilane is part of a silicon surface. The reaction uses UV irradiation and is usually initiated by an added photoactive compound such as a platinum catalyst." [\:cg, rsc:db] synonym: "photo-hydrosilylation" EXACT [] is_a: RXNO:0000290 ! hydrosilylation [Term] id: RXNO:0000304 name: Julia-Kocienski olefination def: "A carbon-carbon coupling reaction between a tetrazole sulfone and an aldehyde or ketone to give a (typically trans) alkene." [rsc:db] synonym: "Julia-Kocienski coupling" EXACT [] synonym: "Julia-Kocienski reaction" EXACT [] is_a: RXNO:0000479 ! olefination relationship: RXNO:0000423 CHEBI:33641 ! has specified product olefin [Term] id: RXNO:0000305 name: seleno-Pummerer rearrangement def: "The conversion of a selenoxide with an alpha-hydrogen to an alpha-subtituted selenoether." [rsc:db] synonym: "selenoxide Pummerer reaction" EXACT [] is_a: RXNO:0000220 ! Pummerer rearrangement [Term] id: RXNO:0000306 name: intramolecular Heck reaction def: "A carbon-carbon coupling reaction where an organohalide or triflate couples to an alkene in the same molecule, catalysed by palladium." [rsc:db] synonym: "intramolecular Heck-Mizoroki" EXACT [] is_a: RXNO:0000005 ! ring formation reaction step relationship: RXNO:0000425 CHEBI:33363 ! has_catalyst palladium [Term] id: RXNO:0000307 name: Mori-Ban indole synthesis def: "An intramolecular Heck reaction of an ortho-halo-aniline with an alkene, catalysed by palladium." [rsc:db] synonym: "Mori-Ban indole reaction" EXACT [] is_a: RXNO:0000395 ! indole synthesis relationship: RXNO:0000423 CHEBI:24828 ! has specified product indoles relationship: RXNO:0000424 CHEBI:33641 ! has specified reactant olefin relationship: RXNO:0000425 CHEBI:33363 ! has_catalyst palladium [Term] id: RXNO:0000308 name: Yamaguchi lactonisation def: "The intramolecular esterification of a carboxylic acid group with an alcohol group using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent) - an intramolecular Yamaguchi esterification." [rsc:db] synonym: "Yamaguchi lactonization" EXACT [] is_a: RXNO:0000309 ! Yamaguchi esterification is_a: RXNO:0000346 ! oxacycle synthesis relationship: RXNO:0000423 CHEBI:25000 ! has specified product lactone [Term] id: RXNO:0000309 name: Yamaguchi esterification def: "The esterification of a carboxylic acid with an alcohol using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent)." [rsc:db] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000479/ is_a: RXNO:0000331 ! substitution step [Term] id: RXNO:0000310 name: oxa-Diels-Alder reaction def: "A Diels-Alder reaction between a diene and an aldehyde or ketone to give a six-membered oxygen-containing ring compound." [rsc:db] synonym: "oxa-Diels-Alder cycloaddition" EXACT [] synonym: "oxa Diels-Alder cycloaddition" EXACT [] synonym: "oxo-Diels-Alder cycloaddition" EXACT [] synonym: "oxo Diels-Alder cycloaddition" EXACT [] synonym: "oxo-Diels-Alder reaction" EXACT [] synonym: "oxo Diels-Alder reaction" EXACT [] synonym: "oxa Diels-Alder reaction" EXACT [] is_a: RXNO:0000313 ! hetero-Diels-Alder reaction [Term] id: RXNO:0000311 name: Tsuji-Trost reaction def: "A carbon-carbon coupling reaction in which a nucleophile reacts with an allyl acetate, allyl halide, allyl carbonate, allyl carbamate, allyl phosphate, allyl sulfone or allyl nitro compound to give an allyl compound. The reaction is catalsed by Pd(0)." [rsc:db] synonym: "Trost allylation" EXACT [] is_a: MOP:0000422 ! allylation is_a: RXNO:0000002 ! carbon-carbon coupling reaction [Term] id: RXNO:0000312 name: Clauson-Kaas reaction def: "A ring rearrangement reaction where an amine reacts with a 2,5-dialkoxytetrahydrofuran to give a pyrrole." [http://www.clauson-kaas.com/cgi-files/mdmgfx/file-709-116554-7465.pdf] synonym: "Clauson-Kaas pyrrole synthesis" EXACT [] is_a: RXNO:0000202 ! ring rearrangement is_a: RXNO:0000497 ! pyrrole synthesis relationship: RXNO:0000423 CHEBI:26455 ! has specified product pyrroles [Term] id: RXNO:0000313 name: hetero-Diels-Alder reaction def: "A [4+2] cycloaddition reaction where a diene (or heterocyclic analogue) reacts with a dienophile to form an unsaturated heterocyclic six-membered ring compound." [rsc:djb] is_a: RXNO:0000006 ! Diels-Alder reaction [Term] id: RXNO:0000316 name: palladium-catalysed carbon-carbon coupling reaction def: "A carbon-carbon coupling reaction that is catalysed by a palladium atom." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000002 ! carbon-carbon coupling reaction intersection_of: RXNO:0000002 ! carbon-carbon coupling reaction intersection_of: RXNO:0000425 CHEBI:33363 ! has_catalyst palladium relationship: RXNO:0000425 CHEBI:33363 ! has_catalyst palladium [Term] id: RXNO:0000317 name: ester condensation reaction xref: NAMERXN:3.6 is_a: MOP:0000627 ! condensation reaction intersection_of: MOP:0000627 ! condensation reaction intersection_of: BFO:0000077 CHEBI:33308 ! has participant beginning to exist carboxylic ester relationship: BFO:0000077 CHEBI:33308 ! has participant beginning to exist carboxylic ester [Term] id: RXNO:0000320 name: amino group deprotection def: "A deprotection reaction where the reactive centre is an amino nitrogen atom." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000203 ! deprotection reaction intersection_of: RXNO:0000203 ! deprotection reaction intersection_of: RXNO:0000417 CHEBI:46882 ! deprotects amino group relationship: RXNO:0000417 CHEBI:46882 ! deprotects amino group [Term] id: RXNO:0000321 name: amino group protection def: "A protection reaction where the reactive centre is an amino nitrogen atom." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000078 ! protection reaction intersection_of: RXNO:0000078 ! protection reaction intersection_of: RXNO:0000416 CHEBI:46882 ! protects amino group relationship: RXNO:0000416 CHEBI:46882 ! protects amino group [Term] id: RXNO:0000322 name: benzylamine protection def: "An amino group protection where the amino nitrogen atom is protected by reaction with benzylamine." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000321 ! amino group protection [Term] id: RXNO:0000323 name: hydroxyl group protection def: "A protection reaction where the reactive centre is a hydroxyl oxygen atom." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000078 ! protection reaction intersection_of: RXNO:0000078 ! protection reaction intersection_of: RXNO:0000416 CHEBI:43176 ! protects hydroxy group relationship: RXNO:0000416 CHEBI:43176 ! protects hydroxy group [Term] id: RXNO:0000324 name: benzyl ether protection def: "A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a benzyl ether." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000323 ! hydroxyl group protection relationship: RXNO:0000416 CHEBI:43176 ! protects hydroxy group [Term] id: RXNO:0000325 name: carboxylic acid protection def: "A protection reaction where the reactive centre is a carboxy oxygen." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000078 ! protection reaction intersection_of: RXNO:0000078 ! protection reaction intersection_of: RXNO:0000416 CHEBI:46883 ! protects carboxy group relationship: RXNO:0000416 CHEBI:46883 ! protects carboxy group [Term] id: RXNO:0000326 name: Boc deprotection def: "An amino group deprotection reaction where a tertbutoxycarbonyl group is removed in acid conditions." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000320 ! amino group deprotection [Term] id: RXNO:0000327 name: benzylamine deprotection def: "An amino group deprotection reaction where a benzylamine group is removed by hydrogenation." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000589 ! hydrogenation is_a: RXNO:0000320 ! amino group deprotection relationship: RXNO:0000417 CHEBI:46882 ! deprotects amino group [Term] id: RXNO:0000328 name: silyl protection def: "A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a silyl ether." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0003339 ! O-silylation is_a: RXNO:0000323 ! hydroxyl group protection [Term] id: RXNO:0000329 name: planned synthesis def: "An experimental procedure with the aim of producing a portion of a given compound or mixture." [http://orcid.org/0000-0001-5985-7429] is_a: OBI:0000011 ! planned process [Term] id: RXNO:0000330 name: acetate protection def: "A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of an acetate ester." [http://orcid.org/0000-0001-5985-7429] synonym: "O-Ac protection" EXACT [] is_a: RXNO:0000323 ! hydroxyl group protection [Term] id: RXNO:0000331 name: substitution step def: "A functional modification step in which one singly-bonded substituent, but not a hydrogen, is replaced by another singly-bonded substituent." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000010 ! functional modification intersection_of: RXNO:0000010 ! functional modification intersection_of: OBI:0000417 RXNO:0000468 ! achieves_planned_objective molecular substitution objective relationship: OBI:0000417 RXNO:0000468 ! achieves_planned_objective molecular substitution objective [Term] id: RXNO:0000332 name: aromatic substitution step def: "A substitution step where one singly-bonded substituent on an aromatic skeleton is replaced by another singly-bonded substituent." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000331 ! substitution step relationship: has_part MOP:0000791 ! aromatic substitution [Term] id: RXNO:0000333 name: Sandmeyer halogenation def: "An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) halide to form an aromatic halide." [RSC:db] is_a: RXNO:0000021 ! Sandmeyer reaction relationship: has_part MOP:0000550 ! halogenation [Term] id: RXNO:0000334 name: Sandmeyer pseudohalogenation def: "An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(II) pseudohalide to form an aromatic pseudohalide." [RSC:db] is_a: RXNO:0000021 ! Sandmeyer reaction relationship: has_part MOP:0000596 ! pseudohalogenation [Term] id: RXNO:0000335 name: reductive amination def: "A functional group modification where a carbonyl oxygen is replaced by an amine." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:1.2 is_a: MOP:0000650 ! amination is_a: RXNO:0000011 ! functional group modification created_by: batchelorc creation_date: 2012-03-22T12:15:29Z [Term] id: RXNO:0000337 name: nitro reduction to amine def: "A reduction reaction where a nitro group is reduced to an amino group." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:7.1 is_a: MOP:0000569 ! reduction is_a: RXNO:0000011 ! functional group modification intersection_of: MOP:0000569 ! reduction intersection_of: RXNO:0000423 CHEBI:32877 ! has specified product primary amine intersection_of: RXNO:0000424 CHEBI:35715 ! has specified reactant nitro compound relationship: OBI:0000417 RXNO:0000453 ! achieves_planned_objective functional group modification objective relationship: RXNO:0000423 CHEBI:32877 ! has specified product primary amine relationship: RXNO:0000424 CHEBI:35715 ! has specified reactant nitro compound created_by: batchelorc creation_date: 2012-03-22T12:28:47Z [Term] id: RXNO:0000338 name: amide reduction to amine def: "A reduction process where an amide is transformed into an amine." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:7.2 is_a: MOP:0000569 ! reduction is_a: RXNO:0000011 ! functional group modification intersection_of: MOP:0000569 ! reduction intersection_of: RXNO:0000423 CHEBI:32952 ! has specified product amine intersection_of: RXNO:0000424 CHEBI:32988 ! has specified reactant amide relationship: OBI:0000417 RXNO:0000453 ! achieves_planned_objective functional group modification objective relationship: RXNO:0000423 CHEBI:32952 ! has specified product amine relationship: RXNO:0000424 CHEBI:32988 ! has specified reactant amide created_by: batchelorc creation_date: 2012-03-22T12:29:51Z [Term] id: RXNO:0000339 name: alkene reduction to alkane def: "A hydrogenation reaction where an alkene is reduced to an alkane." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:7.6 is_a: MOP:0000589 ! hydrogenation created_by: batchelorc creation_date: 2012-03-22T12:30:40Z [Term] id: RXNO:0000340 name: amide N-alkylation def: "An N-alkylation where the reactive centre is an amide nitrogen." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:1.4 is_a: MOP:0002369 ! N-alkylation created_by: batchelorc creation_date: 2012-03-22T03:07:17Z [Term] id: RXNO:0000341 name: aniline N-alkylation def: "An N-alkylation where the reactive centre is an aniline nitrogen." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:1.5 is_a: MOP:0002369 ! N-alkylation created_by: batchelorc creation_date: 2012-03-22T03:07:44Z [Term] id: RXNO:0000342 name: nitrile reduction to amine def: "A reduction where a nitrile is replaced by an amine function." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000569 ! reduction created_by: batchelorc creation_date: 2012-03-22T03:12:31Z [Term] id: RXNO:0000343 name: imine reduction to amine def: "A reduction reaction where an imine function is replaced by an amine." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000569 ! reduction created_by: batchelorc creation_date: 2012-03-22T03:13:12Z [Term] id: RXNO:0000344 name: alkene oxidative cleavage def: "An alkene oxidation where the carbon--carbon double bond is cleaved." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:1.6 is_a: MOP:0000581 ! alkene oxidation created_by: batchelorc creation_date: 2012-03-22T03:15:25Z [Term] id: RXNO:0000345 name: heteroaryl N-alkylation def: "An N-alkylation reaction where the reactive centre is an azacycle ring nitrogen." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:1.1 is_a: MOP:0002369 ! N-alkylation created_by: batchelorc creation_date: 2012-03-22T03:22:27Z [Term] id: RXNO:0000346 name: oxacycle synthesis def: "A ring formation reaction where the intended product contains an oxacycle that was not in any of the reactants." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:4.2 is_a: RXNO:0000349 ! heterocycle synthesis intersection_of: MOP:0000543 ! molecular process intersection_of: RXNO:0000423 CHEBI:38104 ! has specified product oxacycle relationship: RXNO:0000423 CHEBI:38104 ! has specified product oxacycle created_by: batchelorc creation_date: 2012-03-22T03:24:06Z [Term] id: RXNO:0000347 name: azacycle synthesis def: "A ring formation reaction where the intended product contains an azacycle that was not in any of the reactants." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:4.1 is_a: RXNO:0000349 ! heterocycle synthesis intersection_of: MOP:0000543 ! molecular process intersection_of: RXNO:0000423 CHEBI:38101 ! has specified product azacycle relationship: RXNO:0000423 CHEBI:38101 ! has specified product azacycle created_by: batchelorc creation_date: 2012-03-22T03:24:12Z [Term] id: RXNO:0000348 name: thiacycle synthesis def: "A ring formation reaction where the intended product contains an thiacycle that was not in any of the reactants." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:4.3 is_a: RXNO:0000349 ! heterocycle synthesis intersection_of: MOP:0000543 ! molecular process intersection_of: RXNO:0000423 CHEBI:38106 ! has specified product organosulfur heterocyclic compound relationship: RXNO:0000423 CHEBI:38106 ! has specified product organosulfur heterocyclic compound created_by: batchelorc creation_date: 2012-03-22T03:24:23Z [Term] id: RXNO:0000349 name: heterocycle synthesis def: "A ring formation reaction where the intended product contains a heterocycle that was not in any of the reactants." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:4 is_a: RXNO:0000005 ! ring formation reaction step intersection_of: MOP:0000543 ! molecular process intersection_of: RXNO:0000423 CHEBI:5686 ! has specified product heterocyclic compound relationship: RXNO:0000423 CHEBI:5686 ! has specified product heterocyclic compound created_by: batchelorc creation_date: 2012-03-22T03:24:34Z [Term] id: RXNO:0000350 name: alkyne reduction to alkane def: "A hydrogenation reaction where an alkyne is reduced to an alkane." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:7.7 is_a: MOP:0000589 ! hydrogenation created_by: batchelorc creation_date: 2012-03-22T03:30:01Z [Term] id: RXNO:0000351 name: aryl reduction to cycloalkyl def: "A hydrogenation reaction where an aryl ring is reduced to a cycloalkyl ring." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000589 ! hydrogenation created_by: batchelorc creation_date: 2012-03-22T03:30:50Z [Term] id: RXNO:0000352 name: heteroaryl reduction to saturated heterocycle def: "A hydrogenation reaction where a heteroaryl is reduced to a saturated heterocycle." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000589 ! hydrogenation created_by: batchelorc creation_date: 2012-03-22T03:31:49Z [Term] id: RXNO:0000353 name: alcohol oxidation to carboxylic acid def: "An alcohol oxidation where the alcohol centre is replaced with a carboxy group." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000572 ! alcohol oxidation created_by: batchelorc creation_date: 2012-03-22T03:34:20Z [Term] id: RXNO:0000354 name: benzylic oxidation def: "An oxidation reaction where a carbon centre bonded to the benzene ring is oxidized to a carboxyl group." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000568 ! oxidation created_by: batchelorc creation_date: 2012-03-22T03:37:52Z [Term] id: RXNO:0000355 name: allylic oxidation def: "An oxidation reaction where an allylic C-H bond is replaced by a C=O bond." [http://www.chemtube3d.com/ox_se_allylic.html, http://orcid.org/0000-0001-5985-7429] comment: This can be done with, for instance, selenium dioxide. is_a: MOP:0000568 ! oxidation created_by: batchelorc creation_date: 2012-03-22T03:39:47Z [Term] id: RXNO:0000356 name: Jones oxidation def: "An oxidation reaction where an alcohol is oxidized to the corresponding carbonyl compound by a dichromate ion." [http://www.chemtube3d.com/ox_jones_oxidation.html, http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000572 ! alcohol oxidation is_a: RXNO:0000012 ! functional group oxidation created_by: batchelorc creation_date: 2012-03-22T03:39:47Z [Term] id: RXNO:0000357 name: N-acylation to amide def: "An acylation reaction where a nitrogen atom is acylated to form an amide." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:2.1 is_a: MOP:0002479 ! N-acylation created_by: batchelorc creation_date: 2012-03-22T03:39:47Z [Term] id: RXNO:0000358 name: N-acylation to urea def: "An acylation reaction where a nitrogen atom is acylated to form a urea." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:2.3 is_a: MOP:0002479 ! N-acylation created_by: batchelorc creation_date: 2012-03-22T03:39:47Z [Term] id: RXNO:0000359 name: N-acylation to carbamate def: "An N-acylation reaction where a nitrogen centre is acylated to form a carbamate." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:2.4 is_a: MOP:0002479 ! N-acylation created_by: batchelorc creation_date: 2012-03-22T04:09:47Z [Term] id: RXNO:0000360 name: O-acylation to ester def: "An O-acylation reaction where an oxygen centre is acylated to result in an ester." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:2.6 is_a: MOP:0003479 ! O-acylation created_by: batchelorc creation_date: 2012-03-22T04:10:47Z [Term] id: RXNO:0000361 name: Pinner reaction def: "A functional group modification where a nitrile reacts with an alcohol under acid catalysis to form an amidine or ester." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000011 ! functional group modification relationship: has_part RXNO:0000362 ! nitrile alcoholysis [Term] id: RXNO:0000362 name: nitrile alcoholysis def: "An oxidation reaction where a nitrile reacts with an alcohol to form an alkyl imidate." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000568 ! oxidation [Term] id: RXNO:0000363 name: amide to imidoyl chloride conversion def: "A functional group modification where an amide is converted to an imidoyl chloride." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:9.2 is_a: RXNO:0000011 ! functional group modification relationship: RXNO:0000424 CHEBI:32988 ! has specified reactant amide created_by: batchelorc creation_date: 2012-03-22T05:04:20Z [Term] id: RXNO:0000364 name: alcohol to halide conversion def: "A functional group modification where an alcohol is converted to a halide." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:9.1 is_a: RXNO:0000011 ! functional group modification created_by: batchelorc creation_date: 2012-03-22T05:05:15Z [Term] id: RXNO:0000365 name: carboxylic acid to acid chloride conversion def: "A functional group modification where a carboxylic acid is converted to an acid chloride." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:9.3 is_a: RXNO:0000011 ! functional group modification created_by: batchelorc creation_date: 2012-03-22T05:06:09Z [Term] id: RXNO:0000366 name: nitrile to acid conversion def: "A functional group modification where a nitrile is transformed into a carboxylic acid." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:9.4 is_a: RXNO:0000011 ! functional group modification created_by: batchelorc creation_date: 2012-03-22T05:12:32Z [Term] id: RXNO:0000367 name: carbonyl compound to imine conversion def: "A functional group modification where a carbonyl compound is converted to an imine." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:9.6 is_a: RXNO:0000011 ! functional group modification created_by: batchelorc creation_date: 2012-03-22T05:17:03Z [Term] id: RXNO:0000368 name: Crabbé homologation def: "Oxidation of an alkene to an allene by heating with formaldehyde, an amine and an inorganic salt." [doi:10.1039/c39790000859, http://orcid.org/0000-0001-5985-7429] synonym: "Crabbe homologation" EXACT [] is_a: MOP:0000581 ! alkene oxidation is_a: RXNO:0000070 ! chain lengthening relationship: BFO:0000057 CHEBI:32952 ! has_participant amine relationship: RXNO:0000423 CHEBI:37602 ! has specified product allenes relationship: RXNO:0000424 CHEBI:16842 ! has specified reactant formaldehyde relationship: RXNO:0000424 CHEBI:32878 ! has specified reactant alkene created_by: batchelorc creation_date: 2014-01-08T13:48:00Z [Term] id: RXNO:0000369 name: Friedel-Crafts reaction def: "A carbon-carbon coupling reaction between an arene and a carbonyl compound (an acylation) or an alkyl compound that can form a carbocation (an alkylation) to form a substituted arene." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:3.10 is_a: RXNO:0000002 ! carbon-carbon coupling reaction relationship: RXNO:0000424 CHEBI:33658 union_of: RXNO:0000045 ! Friedel-Crafts acylation union_of: RXNO:0000046 ! Friedel-Crafts alkylation [Term] id: RXNO:0000370 name: Demko-Sharpless reaction def: "A functional group modification of a nitrile to a 1H-tetrazole by addition of sodium azide." [doi:10.1021/jo010635w, http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000011 ! functional group modification relationship: RXNO:0000423 CHEBI:35689 ! has specified product tetrazoles relationship: RXNO:0000424 CHEBI:18379 ! has specified reactant nitrile relationship: RXNO:0000424 CHEBI:278547 ! has specified reactant sodium azide [Term] id: RXNO:0000371 name: Griess reaction def: "A diazotisation that proceeds by the addition of nitrous acid, nitric acid and water, resulting in a diazonium nitrate salt." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000174/ is_a: RXNO:0000013 ! diazotisation [Term] id: RXNO:0000372 name: heteroaryl N-arylation def: "An N-arylation reaction where the reactive centre is an azacycle ring nitrogen." [http://orcid.org/0000-0001-5985-7429] xref: NAMERXN:1.3 is_a: MOP:0002411 ! N-arylation [Term] id: RXNO:0000373 name: functional group addition step def: "A planned reaction step in which a covalent bond is formed between the molecular skeleton and a functional group and where the skeletal bond order is unchanged." [http://orcid.org/0000-0001-5985-7429] comment: this is not part of David's grand diagram - well spotted Roger xref: NAMERXN:10 is_a: MOP:0000566 ! formation of covalent bond with group is_a: RXNO:0000010 ! functional modification intersection_of: RXNO:0000010 ! functional modification intersection_of: OBI:0000417 RXNO:0000489 ! achieves_planned_objective functional group addition objective relationship: OBI:0000417 RXNO:0000489 ! achieves_planned_objective functional group addition objective [Term] id: RXNO:0000374 name: Chan-Lam coupling def: "Arylation of an amine or an alcohol with an arylboronic acid, stannane or siloxane in air with a copper acetate catalyst." [doi:10.1016/j.tet.2012.06.015] comment: The canonical variant is the N-arylation of an amine with an arylboronic acid. synonym: "Chan-Lam reaction" EXACT [] synonym: "Chan-Lam-Evans coupling" EXACT [] synonym: "Chan-Lam-Evans reaction" EXACT [] is_a: MOP:0000411 ! arylation is_a: RXNO:0000012 ! functional group oxidation [Term] id: RXNO:0000376 name: Eschweiler-Clarke methylation def: "N-methylation of a primary or secondary amine with formic acid and formaldehyde to yield a tertiary amine." [http://orcid.org/0000-0001-5985-7429] synonym: "Eschweiler-Clarke reaction" EXACT [] is_a: MOP:0002364 ! N-methylation is_a: RXNO:0000012 ! functional group oxidation relationship: RXNO:0000423 CHEBI:32876 ! has specified product tertiary amine relationship: RXNO:0000424 CHEBI:16842 ! has specified reactant formaldehyde relationship: RXNO:0000424 CHEBI:32952 ! has specified reactant amine [Term] id: RXNO:0000377 name: Scholl reaction def: "Coupling of two aromatic rings in the presence of a Lewis acid catalyst." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000390/ is_a: RXNO:0000002 ! carbon-carbon coupling reaction relationship: has_part MOP:0000734 ! Lewis acid catalysis [Term] id: RXNO:0000378 name: intramolecular Scholl reaction def: "Scholl reaction within a single molecule to form a larger ring system." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000000 ! molecular skeleton joining reaction is_a: RXNO:0000005 ! ring formation reaction step is_a: RXNO:0000377 ! Scholl reaction [Term] id: RXNO:0000379 name: intermolecular Scholl reaction def: "Scholl reaction between two aromatic molecules to form a single molecule." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000000 ! molecular skeleton joining reaction is_a: RXNO:0000377 ! Scholl reaction [Term] id: RXNO:0000380 name: Robinson annulation def: "Reaction of a cyclohexanone with methyl vinyl ketone to form a fused-ring cyclohexenone. It is a Michael reaction followed by an intramolecular aldol condensation." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000373/ is_a: RXNO:0000052 ! fused-ring-system formation relationship: has_part MOP:0000561 ! cyclization relationship: has_part RXNO:0000009 ! Michael addition relationship: has_part RXNO:0000017 ! aldol condensation [Term] id: RXNO:0000381 name: Tiffeneau-Demjanov rearrangement def: "Rearrangement of a beta-amino alcohol to yield a carbonyl compound. In the first step the amine is diazotised by reaction with nitrous acid." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000432/ is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000382 name: Demjanov rearrangement def: "Substitution reaction of a primary amine via deazotisation to yield a mixture of the corresponding primary alcohol and secondary alcohol." [http://orcid.org/0000-0001-5985-7429] comment: TODO: Not *entirely* sure how we classify this. Have given it multiple parentage for the now. xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000106/ is_a: RXNO:0000025 ! rearrangement step is_a: RXNO:0000331 ! substitution step [Term] id: RXNO:0000384 name: cyclic alpha-haloketone Favorskii rearrangement def: "Base-catalysed rearrangement of a cyclic alpha-haloketone to the ring-contracted cyclic carboxylic acid." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000206 ! ring contraction is_a: RXNO:0000385 ! Favorskii rearrangement [Term] id: RXNO:0000385 name: Favorskii rearrangement def: "Base-catalysed rearrangement of an alpha-haloketone to a carboxylic acid or ester or amide." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000386 name: Wallach degradation def: "Favorskii rearrangement of a cyclic alpha-dibromoketone followed by decarboxylation to yield a ring-contracted cyclic ketone." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000206 ! ring contraction relationship: has_part MOP:0001713 ! decarboxylation relationship: has_part RXNO:0000384 ! cyclic alpha-haloketone Favorskii rearrangement [Term] id: RXNO:0000387 name: Seyferth-Gilbert homologation def: "Reaction of a carbonyl compound with a dimethyl diazomethyl phosphonate under basic conditions to yield an alkyne." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000395/ is_a: MOP:0000714 ! carbonyl oxidation to alkyne [Term] id: RXNO:0000388 name: Seyferth-Gilbert aldehyde homologation def: "Reaction of an aldehyde with a dimethyl diazomethyl phosphonate under basic conditions to yield a terminal alkyne." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000070 ! chain lengthening is_a: RXNO:0000387 ! Seyferth-Gilbert homologation relationship: RXNO:0000423 CHEBI:73477 ! has specified product terminal acetylenic compound relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde [Term] id: RXNO:0000389 name: Seyferth-Gilbert ketone homologation def: "Reaction of a ketone with a dimethyl diazomethyl phosphonate under basic conditions to yield a terminal alkyne." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000030 ! molecular skeleton insertion reaction is_a: RXNO:0000387 ! Seyferth-Gilbert homologation relationship: RXNO:0000423 CHEBI:73477 ! has specified product terminal acetylenic compound [Term] id: RXNO:0000390 name: Seyferth-Gilbert-Bestmann homologation def: "Seyferth-Gilbert aldehyde homologation where the Seyferth-Gilbert reagent is generated in situ by reaction with methanol and potassium carbonate." [http://orcid.org/0000-0001-5985-7429] synonym: "Bestmann modification" EXACT [] synonym: "Ohira-Bestmann homologation" EXACT [] synonym: "Ohira-Bestmann modification" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000395/ is_a: RXNO:0000388 ! Seyferth-Gilbert aldehyde homologation relationship: RXNO:0000423 CHEBI:17478 ! has specified product aldehyde [Term] id: RXNO:0000391 name: Knorr pyrazole synthesis def: "Synthesis of a pyrazole by condensation of a 1,3-dicarbonyl compound with a hydrazine, hydrazide, semicarbazide or aminoguanidine." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000233/ is_a: MOP:0000628 ! molecular dehydration reaction is_a: RXNO:0000392 ! pyrazole synthesis [Term] id: RXNO:0000392 name: pyrazole synthesis def: "A reaction in which the intended product is a pyrazole that was not present in any of the reactants." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000347 ! azacycle synthesis intersection_of: RXNO:0000347 ! azacycle synthesis intersection_of: RXNO:0000423 CHEBI:26410 ! has specified product pyrazoles relationship: RXNO:0000423 CHEBI:26410 ! has specified product pyrazoles [Term] id: RXNO:0000393 name: quinoline synthesis def: "A reaction in which the intended product is a quinoline that was not present in any of the reactants." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000052 ! fused-ring-system formation is_a: RXNO:0000347 ! azacycle synthesis intersection_of: MOP:0000543 ! molecular process intersection_of: RXNO:0000423 CHEBI:26513 ! has specified product quinolines relationship: RXNO:0000423 CHEBI:26513 ! has specified product quinolines [Term] id: RXNO:0000394 name: Knorr quinoline synthesis def: "Synthesis of an alpha-hydroxyquinoline by reaction of a beta-ketoester and an arylamine then dehydration with concentrated sulfuric acid." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000234/ is_a: RXNO:0000393 ! quinoline synthesis relationship: has_part MOP:0000628 ! molecular dehydration reaction [Term] id: RXNO:0000395 name: indole synthesis def: "A reaction in which the intended product is an indole that was not present in any of the reactants." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000052 ! fused-ring-system formation is_a: RXNO:0000347 ! azacycle synthesis intersection_of: MOP:0000543 ! molecular process intersection_of: RXNO:0000423 CHEBI:24828 ! has specified product indoles relationship: RXNO:0000423 CHEBI:24828 ! has specified product indoles [Term] id: RXNO:0000396 name: Larock indole synthesis def: "Palladium-catalysed synthesis of a 2,3-substituted indole by reaction of an ortho-iodoaniline with an internal alkyne." [http://orcid.org/0000-0001-5985-7429] synonym: "Larock indolisation" EXACT [] synonym: "Larock indolization" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000250/ is_a: RXNO:0000395 ! indole synthesis relationship: RXNO:0000425 CHEBI:33363 ! has_catalyst palladium [Term] id: RXNO:0000397 name: Pechmann pyrazole synthesis def: "Reaction of an organic diazo compound with an acetylene to yield a pyrazole." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000323/ is_a: RXNO:0000392 ! pyrazole synthesis [Term] id: RXNO:0000398 name: benzimidazole synthesis def: "A reaction in which the intended product is a benzimidazole that was not present in any of the reactants." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000052 ! fused-ring-system formation relationship: RXNO:0000423 CHEBI:22715 ! has specified product benzimidazoles [Term] id: RXNO:0000399 name: Phillips benzimidazole synthesis def: "Reaction of an ortho-diaminobenzene with a carboxylic acid under heat to yield a benzimidazole." [ISBN:9780080534459, http://orcid.org/0000-0001-5985-7429] comment: This may be done in the presence of an acid, hexamethyldisilazane in the presence of catalytic triflic acid, a titanium catalyst, elevated pressure, or under UV. [ISBN:9780080534459] synonym: "Phillips benzimidazole condensation" EXACT [] is_a: RXNO:0000398 ! benzimidazole synthesis [Term] id: RXNO:0000400 name: pyrimidine synthesis def: "A reaction in which the intended product is a pyrimidine that was not present in any of the reactants." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000347 ! azacycle synthesis relationship: RXNO:0000423 CHEBI:39447 ! has specified product pyrimidines [Term] id: RXNO:0000401 name: triazine synthesis def: "A reaction in which the intended product is a triazine that was not present in any of the reactants." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000347 ! azacycle synthesis relationship: RXNO:0000423 CHEBI:26588 ! has specified product triazines [Term] id: RXNO:0000402 name: Pinner pyrimidine synthesis def: "Reaction of a 1,3-dicarbonyl compound with an amidine to yield a pyrimidine." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000400 ! pyrimidine synthesis relationship: has_part MOP:0000628 ! molecular dehydration reaction [Term] id: RXNO:0000403 name: Pinner triazine synthesis def: "Reaction of aryl amidines or halogenated aliphatics amidines with phosgene to yield a 2-hydroxy-4,6-diaryl-s-triazine with loss of ammonia." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000343/ is_a: RXNO:0000401 ! triazine synthesis [Term] id: RXNO:0000404 name: oxa-Pictet-Spengler reaction def: "Cyclisation-condensation of a beta-arylethanol with an aldehyde to yield an ortho-,peri-fused aryl-oxacycle." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000627 ! condensation reaction is_a: RXNO:0000052 ! fused-ring-system formation is_a: RXNO:0000346 ! oxacycle synthesis relationship: RXNO:0000423 CHEBI:38104 ! has specified product oxacycle relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde [Term] id: RXNO:0000405 name: Prilezhaev epoxidation def: "Epoxidation of an alkene by reaction with a peroxy acid." [http://orcid.org/0000-0001-5985-7429] synonym: "Prileschajew reaction" EXACT [] synonym: "Prilezhaev reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000351/ is_a: MOP:0000671 ! epoxidation is_a: RXNO:0000346 ! oxacycle synthesis relationship: RXNO:0000423 CHEBI:32955 ! has specified product epoxide [Term] id: RXNO:0000406 name: Appel halogenation def: "Conversion of an alcohol to an alkyl halide with triphenylphosphine and a halide source." [doi:10.1002/anie.197508011, http://orcid.org/0000-0001-5985-7429] synonym: "Appel reaction" EXACT [] is_a: RXNO:0000364 ! alcohol to halide conversion relationship: RXNO:0000423 CHEBI:24469 ! has specified product haloalkane relationship: RXNO:0000424 CHEBI:30879 ! has specified reactant alcohol relationship: RXNO:0000424 CHEBI:36601 ! has specified reactant triphenylphosphane oxide [Term] id: RXNO:0000407 name: Appel iodination def: "Conversion of an alcohol to an alkyl iodide with triphenylphosphine and tetraiodomethane." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000406 ! Appel halogenation relationship: RXNO:0000423 CHEBI:37757 ! has specified product iodoalkane [Term] id: RXNO:0000408 name: Appel chlorination def: "Conversion of an alcohol to an alkyl chloride with triphenylphosphine and tetrachloromethane." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000406 ! Appel halogenation relationship: RXNO:0000423 CHEBI:23128 ! has specified product chloroalkane relationship: RXNO:0000424 CHEBI:27385 ! has specified reactant tetrachloromethane [Term] id: RXNO:0000409 name: Appel bromination def: "Conversion of an alcohol to an alkyl bromide with triphenylphosphine and tetrabromomethane or bromine." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000406 ! Appel halogenation union_of: RXNO:0000554 ! Appel bromination with tetrabromomethane union_of: RXNO:0000555 ! Appel bromination with bromine relationship: RXNO:0000423 CHEBI:22929 ! has specified product bromoalkane [Term] id: RXNO:0000410 name: Hofmann rearrangement def: "Rearrangement of a primary carboxylic amide to an isocyanate." [http://orcid.org/0000-0001-5985-7429] comment: This counts as an end-of-chain chain shortening because the terminal carbon is separated from the skeleton into the isocyanate group. is_a: RXNO:0000105 ! end-of-chain chain shortening [Term] id: RXNO:0000411 name: Hofmann reaction def: "Conversion of a primary carboxylic amide to the lower homologue primary amine. The first step is the Hofmann rearrangement" [http://orcid.org/0000-0001-5985-7429] synonym: "Hofmann degradation" RELATED [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000209/ is_a: RXNO:0000105 ! end-of-chain chain shortening relationship: has_part RXNO:0000410 ! Hofmann rearrangement [Term] id: RXNO:0000412 name: Newman-Kwart rearrangement def: "Rearrangement of an O-aryl thiocarbamate to an S-aryl thiocarbamate by migration of the aryl group." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000011 ! functional group modification [Term] id: RXNO:0000413 name: Zincke nitration def: "Substitution of phenol ortho- or para-bromo or iodo groups by a nitro group on treatment with nitrous acid or a nitrite in acetic acid." [https://www.rsc.org/Merck-Index/reaction/rxn1500000484/] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000484/ is_a: MOP:0000556 ! nitration is_a: RXNO:0000332 ! aromatic substitution step [Term] id: RXNO:0000414 name: haloethanoate ester-aldehyde Darzens reaction def: "A coupling of an aldehyde with an alpha-haloethanoate ester to form the next homologous aldehyde." [http://orcid.org/0000-0001-5985-7429] comment: These are not necessary-and-sufficient conditions because we can't say "one longer" in OWL. is_a: RXNO:0000070 ! chain lengthening is_a: RXNO:0000077 ! Darzens reaction relationship: RXNO:0000423 CHEBI:17478 ! has specified product aldehyde relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde [Term] id: RXNO:0000415 name: haloethanoate ester-ketone Darzens reaction def: "A coupling of a ketone with an alpha-haloethanoate ester to replace the oxo group with a formyl group." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000077 ! Darzens reaction relationship: RXNO:0000423 CHEBI:17478 ! has specified product aldehyde relationship: RXNO:0000424 CHEBI:17087 ! has specified reactant ketone [Term] id: RXNO:0000418 name: phthalimide protection def: "Protection of a primary amino group by reaction with phthalic anhydride." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000321 ! amino group protection relationship: RXNO:0000416 CHEBI:46882 ! protects amino group relationship: RXNO:0000424 CHEBI:36605 ! has specified reactant phthalic anhydride [Term] id: RXNO:0000419 name: phthalimide deprotection def: "Conversion of a phthalimide into the corresponding primary amine." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000320 ! amino group deprotection relationship: RXNO:0000417 CHEBI:46882 ! deprotects amino group [Term] id: RXNO:0000420 name: Kröhnke pyridine synthesis def: "Condensation of a 1,5-diketone with ammonium acetate in acetic acid to form a pyridine." [http://orcid.org/0000-0001-5985-7429] synonym: "Krohnke pyridine synthesis" EXACT [] xref: http://dx.doi.org/10.1039/SP543 is_a: RXNO:0000520 ! pyridine synthesis relationship: RXNO:0000423 CHEBI:26421 ! has specified product pyridines [Term] id: RXNO:0000421 name: Gattermann chlorination def: "A Gattermann halogenation where the aryl diazonium salt reacts with copper powder and hydrochloric acid to yield an aromatic chloride." [http://orcid.org/0000-0002-4077-4719] is_a: RXNO:0000022 ! Gattermann halogenation relationship: RXNO:0000424 CHEBI:17883 ! has specified reactant hydrogen chloride [Term] id: RXNO:0000422 name: Gattermann bromination def: "A Gattermann halogenation where the aryl diazonium salt reacts with copper powder and hydrobromic acid to yield an aromatic bromide." [http://orcid.org/0000-0002-4077-4719] is_a: RXNO:0000022 ! Gattermann halogenation relationship: RXNO:0000424 CHEBI:47266 ! has specified reactant hydrogen bromide [Term] id: RXNO:0000426 name: aldehyde Barbier reaction def: "A joining reaction between an aldehyde and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a secondary alcohol." [http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000084 ! Barbier reaction relationship: RXNO:0000423 CHEBI:35681 ! has specified product secondary alcohol [Term] id: RXNO:0000427 name: ketone Barbier reaction def: "A joining reaction between an ketone and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a tertiary alcohol." [http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000084 ! Barbier reaction relationship: RXNO:0000423 CHEBI:26878 ! has specified product tertiary alcohol [Term] id: RXNO:0000428 name: pivaloyl protection def: "Protection of a hydroxy group by reaction with pivaloyl chloride, resulting in formation of a pivaloyl ester." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000323 ! hydroxyl group protection relationship: RXNO:0000423 CHEBI:50784 ! has specified product pivalate ester [Term] id: RXNO:0000429 name: pivaloyl deprotection def: "A hydroxy group deprotection where a pivalate group is removed in acid or base conditions." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000430 ! hydroxy group deprotection relationship: RXNO:0000417 CHEBI:43176 ! deprotects hydroxy group relationship: RXNO:0000424 CHEBI:50784 ! has specified reactant pivalate ester [Term] id: RXNO:0000430 name: hydroxy group deprotection def: "A deprotection reaction where the reactive centre is an oxygen atom." [http://orcid.org/0000-0001-5985-7429] synonym: "alcohol deprotection" EXACT [] is_a: RXNO:0000203 ! deprotection reaction intersection_of: RXNO:0000203 ! deprotection reaction intersection_of: RXNO:0000417 CHEBI:43176 ! deprotects hydroxy group relationship: RXNO:0000417 CHEBI:43176 ! deprotects hydroxy group [Term] id: RXNO:0000431 name: carboxylic acid to primary alcohol reduction def: "A carboxylic acid reduction where the product is the corresponding primary alcohol." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000569 ! reduction relationship: BFO:0000077 CHEBI:15734 ! has participant beginning to exist primary alcohol relationship: BFO:0000078 CHEBI:33575 ! has participant ceasing to exist carboxylic acid [Term] id: RXNO:0000432 name: tert-butyl protection def: "A carboxy group protection where the product is a tert-butyl ester." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000325 ! carboxylic acid protection relationship: RXNO:0000416 CHEBI:46883 ! protects carboxy group [Term] id: RXNO:0000433 name: carboxy group deprotection def: "A deprotection reaction where the reactive centre is a carboxy oxygen atom." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000203 ! deprotection reaction intersection_of: RXNO:0000203 ! deprotection reaction intersection_of: RXNO:0000417 CHEBI:46883 ! deprotects carboxy group relationship: RXNO:0000417 CHEBI:46883 ! deprotects carboxy group [Term] id: RXNO:0000434 name: tert-butyl ester deprotection def: "A deprotection reaction where the reactant is a tert-butyl ester and the product is a carboxylic acid." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000433 ! carboxy group deprotection relationship: RXNO:0000417 CHEBI:46883 ! deprotects carboxy group [Term] id: RXNO:0000435 name: methyl ester deprotection def: "A deprotection reaction where the reactant is a methyl ester and the product is a carboxylic acid." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000433 ! carboxy group deprotection relationship: RXNO:0000417 CHEBI:46883 ! deprotects carboxy group [Term] id: RXNO:0000436 name: ethyl ester deprotection def: "A deprotection reaction where the reactant is an ethyl ester and the product is a carboxylic acid." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000433 ! carboxy group deprotection relationship: RXNO:0000417 CHEBI:46883 ! deprotects carboxy group [Term] id: RXNO:0000437 name: molecular transformation objective def: "An objective specification that describes how a molecule's skeleton and substituents are to be transformed by a given experiment." [http://orcid.org/0000-0001-5985-7429] is_a: IAO:0000005 ! objective specification [Term] id: RXNO:0000438 name: molecular skeleton cleaving objective def: "A molecular transformation specification that specifies that atoms should be lost from the molecular skeleton." [RSC:db] is_a: RXNO:0000437 ! molecular transformation objective [Term] id: RXNO:0000439 name: molecular ring formation objective def: "A molecular transformation specification that specifies that the product should contain a ring that was not in any of the reactants." [RSC:db] is_a: RXNO:0000437 ! molecular transformation objective [Term] id: RXNO:0000440 name: molecular skeleton joining objective def: "A molecular transformation specification that specifies that atoms should be added to the molecular skeleton." [RSC:db] is_a: RXNO:0000437 ! molecular transformation objective [Term] id: RXNO:0000441 name: molecular rearrangement objective def: "A molecular transformation specification that specifies that the number of rings and number of skeletal atoms should be preserved and that one or more atoms or groups of atoms move from one atom to another." [RSC:db] is_a: RXNO:0000437 ! molecular transformation objective [Term] id: RXNO:0000442 name: functional modification objective def: "A molecular transformation specification that specifies that the substituents of a molecule should be changed but the number of atoms in the skeleton and their connectivity, but not necessarily the bond orders, should remain the same." [RSC:db] is_a: RXNO:0000437 ! molecular transformation objective [Term] id: RXNO:0000443 name: Sakurai reaction def: "Reaction of allyltrimethylsilane with a carbon electrophile to allylate the carbon electrophile." [http://orcid.org/0000-0001-5985-7429] synonym: "Hosomi-Sakurai reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000383/ is_a: MOP:0000422 ! allylation is_a: RXNO:0000002 ! carbon-carbon coupling reaction union_of: RXNO:0000212 ! Sakurai reaction, aldehyde or ketone union_of: RXNO:0000213 ! Sakurai reaction, enone union_of: RXNO:0000214 ! Sakurai reaction, acid chloride union_of: RXNO:0000215 ! Sakurai reaction, acetal or ketal union_of: RXNO:0000216 ! imine Sakurai reaction union_of: RXNO:0000217 ! Sakurai reaction, epoxide [Term] id: RXNO:0000444 name: Fries rearrangement def: "Rearrangement of the acyl group in a phenolate ester to the ortho- and/or para-position. It is catalysed by a Lewis acid." [http://orcid.org/0000-0001-5985-7429] comment: Can be promoted by heat or UV. The UV version (photo-Fries) involves a radical mechanism. synonym: "photo-Fries rearrangement" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000160/ is_a: RXNO:0000025 ! rearrangement step union_of: RXNO:0000445 ! ortho-Fries rearrangement union_of: RXNO:0000446 ! para-Fries rearrangement relationship: has_part MOP:0000734 ! Lewis acid catalysis [Term] id: RXNO:0000445 name: ortho-Fries rearrangement def: "Rearrangement of the acyl group in a phenolate ester to the ortho-position." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000444 ! Fries rearrangement [Term] id: RXNO:0000446 name: para-Fries rearrangement def: "Rearrangement of the acyl group in a phenolate ester to the para-position." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000444 ! Fries rearrangement [Term] id: RXNO:0000447 name: Duff reaction def: "Formylation of a phenol or aromatic amine with hexamethylenetetramine in acidic conditions." [doi:10.1039/jr9410000547, doi:10.1039/JR9450000276] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000119/ is_a: MOP:0000003 ! formylation is_a: RXNO:0000002 ! carbon-carbon coupling reaction relationship: RXNO:0000424 CHEBI:33860 [Term] id: RXNO:0000448 name: molecular chain lengthening objective def: "A molecular skeleton joining adjective that is satisfied by a chain part of a molecular skeleton being lengthened." [RSC:xp] is_a: RXNO:0000440 ! molecular skeleton joining objective [Term] id: RXNO:0000449 name: molecular ring breaking objective def: "A molecular skeleton transformation objective that is satisfied by a reaction where the product has fewer rings than the reactants." [RSC:xp] is_a: RXNO:0000437 ! molecular transformation objective [Term] id: RXNO:0000450 name: molecular ring contraction objective def: "A molecular skeleton transformation objective that is satisfied by a reaction where an existing ring is reduced in size." [RSC:xp] is_a: RXNO:0000437 ! molecular transformation objective [Term] id: RXNO:0000451 name: aldehyde Sakurai reaction def: "A carbon-carbon coupling reaction in which an aldehyde reacts with allyltrimethylsilane to form a homoallylic alcohol." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000212 ! Sakurai reaction, aldehyde or ketone relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde [Term] id: RXNO:0000452 name: ketone Sakurai reaction def: "A carbon-carbon coupling reaction in which a ketone reacts with allyltrimethylsilane to form a homoallylic alcohol." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000212 ! Sakurai reaction, aldehyde or ketone relationship: RXNO:0000424 CHEBI:17087 ! has specified reactant ketone [Term] id: RXNO:0000453 name: functional group modification objective def: "A molecular skeleton transformation objective that is satisfied by a reaction in which a functional group undergoes a change that does not affect the number of atoms in (or connectivity of) the skeleton of the molecule." [RSC:xp] is_a: RXNO:0000442 ! functional modification objective [Term] id: RXNO:0000454 name: end-of-chain chain shortening objective def: "A molecular skeleton transformation objective that is satisfied by a reaction in which a single skeletal atom is removed from the end of a chain." [RSC:xp] is_a: RXNO:0000438 ! molecular skeleton cleaving objective [Term] id: RXNO:0000455 name: functional reduction objective def: "A functional group modification objective that is satisfied by a reaction in which a functional group is reduced." [RSC:xp] is_a: RXNO:0000453 ! functional group modification objective [Term] id: RXNO:0000456 name: addition objective def: "A functional modification objective that is satisfied by a reaction in which two or more groups of atoms are added to the molecule, resulting in a change of skeletal bond order." [RSC:xp] is_a: RXNO:0000442 ! functional modification objective [Term] id: RXNO:0000457 name: molecular ring expansion objective def: "A molecular transformation objective that is satisfied by a reaction in which an existing skeletal ring is increased in size." [RSC:xp] is_a: RXNO:0000437 ! molecular transformation objective [Term] id: RXNO:0000458 name: molecular ring rearrangement objective def: "A molecular transformation objective that is satisfied by a reaction in which the number of skeletal rings in a molecule stays the same but the connectivity of the atoms in at least one ring changes." [RSC:xp] is_a: RXNO:0000437 ! molecular transformation objective [Term] id: RXNO:0000459 name: acetoacetic ester synthesis def: "A carbon-carbon coupling reaction between a beta-ketoester and an alkyl halide to yield an alpha-alkylated ester." [http://orcid.org/0000-0001-5985-7429] comment: Subsequent treatment with mild hydrolysis leads to a ketone; concentrated base produces a substituted ester. xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000001/ is_a: RXNO:0000000 ! molecular skeleton joining reaction relationship: OBI:0000417 RXNO:0000440 ! achieves_planned_objective molecular skeleton joining objective relationship: RXNO:0000423 CHEBI:33308 ! has specified product carboxylic ester relationship: RXNO:0000424 CHEBI:24469 ! has specified reactant haloalkane relationship: RXNO:0000424 CHEBI:51849 ! has specified reactant beta-ketoester [Term] id: RXNO:0000460 name: intramolecular acyloin condensation def: "A reductive coupling reaction between two ester groups in the same molecule to give an acyloin (an alpha-hydroxyketone)." [http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000005 ! ring formation reaction step is_a: RXNO:0000085 ! acyloin condensation relationship: OBI:0000417 RXNO:0000439 ! achieves_planned_objective molecular ring formation objective [Term] id: RXNO:0000461 name: intermolecular acyloin condensation def: "A reductive coupling reaction between two ester groups in different molecules to give an acyloin (an alpha-hydroxyketone)." [http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000085 ! acyloin condensation relationship: OBI:0000417 RXNO:0000440 ! achieves_planned_objective molecular skeleton joining objective [Term] id: RXNO:0000462 name: molecular extrusion objective def: "A molecular transformation objective that is satisfied by a cleaving reaction in which a skeletal atom or group of atoms is removed from the middle of a molecule." [RSC:xp] is_a: RXNO:0000438 ! molecular skeleton cleaving objective [Term] id: RXNO:0000463 name: molecular fragmentation objective def: "A molecular transformation objective that is satisfied by a reaction in which the parent molecule breaks up into three or more products." [RSC:xp] is_a: RXNO:0000438 ! molecular skeleton cleaving objective [Term] id: RXNO:0000464 name: Pauson-Khand reaction def: "A [2+2+1] cycloaddition between an alkyne, an alkene and carbon monoxide to form an alpha-beta-unsaturated cyclopentenone." [doi:10.1039/P19730000975] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000320/ is_a: MOP:0000720 ! [2+2+1] cycloaddition [Term] id: RXNO:0000465 name: fused-ring-system formation objective def: "A molecular transformation objective that is satisfied by a reaction in which a fused ring system is present in a product that was not present in any of the reactants." [RSC:xp] is_a: RXNO:0000439 ! molecular ring formation objective [Term] id: RXNO:0000466 name: polymerisation objective def: "A molecular transformation objective that is satisfied by a reaction in which a large number of monomers react together to product a polymer consisting of repeating units." [RSC:xp] is_a: RXNO:0000440 ! molecular skeleton joining objective [Term] id: RXNO:0000467 name: Algar-Flynn-Oyamada reaction def: "A fused-ring-system formation reaction where a flavonol is produced by oxidation of a chalcone with alkaline hydrogen peroxide." [http://orcid.org/0000-0001-5985-7429] comment: definition source Merck Index xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000005/ is_a: RXNO:0000052 ! fused-ring-system formation is_a: RXNO:0000346 ! oxacycle synthesis relationship: RXNO:0000423 CHEBI:28802 ! has specified product flavonols relationship: RXNO:0000424 CHEBI:16240 ! has specified reactant hydrogen peroxide relationship: RXNO:0000424 CHEBI:23086 ! has specified reactant chalcones [Term] id: RXNO:0000468 name: molecular substitution objective def: "A molecular transformation objective that is satisfied by a reaction in which one singly-bonded substituent, but not a hydrogen, is replaced by another singly-bonded substituent." [RSC:xp] is_a: RXNO:0000442 ! functional modification objective [Term] id: RXNO:0000470 name: Allan-Robinson flavone synthesis def: "Reaction of ortho-hydroxyaryl ketones with aromatic carboxylic acid anhydrides to yield a flavone." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000475 ! Allan-Robinson reaction relationship: RXNO:0000423 CHEBI:24043 ! has specified product flavones relationship: RXNO:0000424 CHEBI:35873 [Term] id: CHEBI:35873 name: carboxylic anhydride is_a: CHEBI:36606 [Term] id: RXNO:0000471 name: Allan-Robinson isoflavone synthesis def: "Reaction of ortho-hydroxyaryl ketones with aromatic carboxylic acid anhydrides to yield an isoflavone." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000475 ! Allan-Robinson reaction relationship: RXNO:0000423 CHEBI:38757 ! has specified product isoflavones relationship: RXNO:0000424 CHEBI:35873 [Term] id: RXNO:0000472 name: Amadori rearrangement def: "Rearrangement of an aldose N-glycoside to a ketose N-glycoside by acid or base catalysis." [http://orcid.org/0000-0001-5985-7429] comment: definition source Merck Index xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000008/ is_a: RXNO:0000025 ! rearrangement step [Term] id: RXNO:0000473 name: Arens-van Dorp synthesis def: "Reaction of a ketone with ethoxyacetylene to form an alkoxyethynyl alcohol." [http://orcid.org/0000-0001-5985-7429] comment: definition source Merck Index xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000009/ is_a: RXNO:0000000 ! molecular skeleton joining reaction [Term] id: RXNO:0000474 name: Auwers synthesis def: "Ring expansion of a 2-bromo-2-(alpha-bromobenzyl)-1-benzofuran to a flavonol in alcoholic alkali." [http://orcid.org/0000-0001-5985-7429] comment: definition source Merck Index xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000011/ is_a: RXNO:0000108 ! ring expansion is_a: RXNO:0000346 ! oxacycle synthesis relationship: RXNO:0000423 CHEBI:28802 ! has specified product flavonols [Term] id: RXNO:0000475 name: Allan-Robinson reaction def: "Reaction of ortho-hydroxyaryl ketones with aromatic acid anhydrides to yield a flavone or isoflavone." [http://orcid.org/0000-0001-5985-7429] comment: definition source Merck Index xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000006/ is_a: RXNO:0000052 ! fused-ring-system formation is_a: RXNO:0000346 ! oxacycle synthesis union_of: RXNO:0000470 ! Allan-Robinson flavone synthesis union_of: RXNO:0000471 ! Allan-Robinson isoflavone synthesis [Term] id: RXNO:0000476 name: Meyer-Schuster rearrangement def: "Rearrangement of a propargyl alcohol to an alpha,beta-unsaturated carbonyl compound via an allene intermediate to yield the gamma-substituted product." [doi:10.1039/b912099h] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000278/ is_a: RXNO:0000025 ! rearrangement step relationship: RXNO:0000469 CHEBI:37602 ! has_intermediate allenes [Term] id: RXNO:0000477 name: Rupe rearrangement def: "Rearrangement of a propargyl alcohol to an alpha,beta-unsaturated carbonyl compound via an enyne intermediate to yield the beta-substituted product." [doi:10.1039/b912099h] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000278/ is_a: RXNO:0000025 ! rearrangement step relationship: RXNO:0000469 CHEBI:59831 ! has_intermediate enyne [Term] id: RXNO:0000478 name: Still-Gennari modification def: "A Horner-Wadsworth-Emmons reaction that uses phosphonates with electron-withdrawing groups and dissociating conditions to produce predominantly Z-olefins." [http://orcid.org/0000-0001-5985-7429] synonym: "Still modification" EXACT [] is_a: RXNO:0000056 ! Horner-Wadsworth-Emmons reaction [Term] id: RXNO:0000479 name: olefination def: "A molecular skeleton joining reaction where the connection formed is a carbon-carbon double bond." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000000 ! molecular skeleton joining reaction intersection_of: RXNO:0000002 ! carbon-carbon coupling reaction intersection_of: RXNO:0000423 CHEBI:33641 ! has specified product olefin relationship: RXNO:0000423 CHEBI:33641 ! has specified product olefin [Term] id: RXNO:0000480 name: Tebbe olefination def: "Reaction of an aldehyde or ketone or carboxylic ester or amide with the Tebbe reagent to yield an olefin or an enol ether or an enamine." [http://orcid.org/0000-0001-5985-7429] comment: definition source Merck Index, heavily modified xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000428/ is_a: RXNO:0000479 ! olefination [Term] id: RXNO:0000481 name: Myers-Saito cyclisation def: "Cyclization of a enynyl allene to yield a toluene biradical with radical centres on the methyl group and at the meta position." [doi:10.1039/b009965l, http://orcid.org/0000-0001-5985-7429] synonym: "Myers-Saito cyclization" EXACT [] synonym: "Myers-Saito process" EXACT [] synonym: "Myers-Saito reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000292/ is_a: RXNO:0000005 ! ring formation reaction step created_by: batchelorc creation_date: 2014-02-28T09:00:00Z [Term] id: RXNO:0000482 name: Schmittel cyclisation def: "Cyclization of a enynyl allene to yield a 1-methyl-5-methylenecyclopenta-1,3-diene biradical with radical centres on the methyl group and methylene group." [doi:10.1039/b009965l, http://orcid.org/0000-0001-5985-7429] synonym: "Schmittel cyclization" EXACT [] is_a: RXNO:0000005 ! ring formation reaction step created_by: batchelorc creation_date: 2014-02-28T09:00:00Z [Term] id: RXNO:0000483 name: Baudisch reaction def: "Copper-catalysed reaction of benzene with a nitrosylating agent and hydrogen peroxide to form an o-nitrosophenol." [http://orcid.org/0000-0001-5985-7429] xref: http://en.wikipedia.org/wiki/Baudisch_reaction xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000026/ is_a: RXNO:0000373 ! functional group addition step created_by: batchelorc creation_date: 2014-02-28T09:00:00Z [Term] id: RXNO:0000484 name: deprotection objective def: "A functional modification objective that is satisfied by deprotecting some functional group." [RSC:xp] is_a: RXNO:0000442 ! functional modification objective created_by: batchelorc creation_date: 2014-02-28T09:00:00Z [Term] id: RXNO:0000485 name: protection objective def: "A functional modification objective that is satisfied by protecting some functional group." [RSC:xp] is_a: RXNO:0000442 ! functional modification objective created_by: batchelorc creation_date: 2014-02-28T09:00:00Z [Term] id: RXNO:0000486 name: molecular skeleton elimination objective def: "A functional modification objective that is satisfied by a reaction in which two or more groups of atoms are removed from the molecule, resulting in a change of skeletal bond order." [RSC:xp] is_a: RXNO:0000442 ! functional modification objective created_by: batchelorc creation_date: 2014-02-28T09:00:00Z [Term] id: RXNO:0000487 name: molecular skeleton insertion objective def: "A molecular skeleton joining objective that is satisfied by a reaction in which one or more atoms are added to the middle of a chain." [RSC:xp] is_a: RXNO:0000440 ! molecular skeleton joining objective created_by: batchelorc creation_date: 2014-02-28T09:00:00Z [Term] id: RXNO:0000488 name: joining with rearrangement objective def: "A molecular skeleton joining objective that is satisfied by a reaction in which one or more atoms are added to the molecular skeleton and a skeletal rearrangement occurs." [RSC:xp] is_a: RXNO:0000440 ! molecular skeleton joining objective created_by: batchelorc creation_date: 2014-02-28T09:00:00Z [Term] id: RXNO:0000489 name: functional group addition objective def: "A functional modification objective that is satisfied by a reaction in which a covalent bond is formed between the molecular skeleton and a functional group and where the skeletal bond order is unchanged." [RSC:xp] is_a: RXNO:0000442 ! functional modification objective created_by: batchelorc creation_date: 2014-02-28T09:00:00Z [Term] id: RXNO:0000490 name: functional oxidation objective def: "A functional group modification objective that is satisfied by a reaction in which a functional group is oxidised." [RSC:xp] is_a: RXNO:0000453 ! functional group modification objective created_by: batchelorc creation_date: 2014-02-28T09:00:00Z [Term] id: RXNO:0000491 name: interrupted Nazarov cyclisation def: "Cyclisation of a propargyl alpha,beta-unsaturated ketone where the reactant rearranges to an allenyl vinyl ketone, followed by a Nazarov cyclisation in which a nucleophile 'intercepts' the intermediate carbocation to yield a cyclopentenone substituted at the alpha position opposite the double bond." [doi:10.1039/c3cs60333d] synonym: "interrupted Nazarov cyclization" EXACT [] is_a: RXNO:0000005 ! ring formation reaction step relationship: has_part RXNO:0000209 ! Nazarov cyclisation created_by: batchelorc creation_date: 2014-02-28T12:00:00Z [Term] id: RXNO:0000492 name: Bamberger rearrangement def: "Rearrangement of an N-phenylhydroxamine in acid to yield a para-aminophenol." [http://orcid.org/0000-0001-5985-7429] comment: definition source Merck Index xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000015/ is_a: RXNO:0000025 ! rearrangement step created_by: batchelorc creation_date: 2014-03-03T09:00:00Z [Term] id: RXNO:0000493 name: Bart reaction def: "Reaction of an aromatic diazonium compound with an alklai arsenite in the presence of copper or silver to yield an aromatic arsonic acid." [http://orcid.org/0000-0001-5985-7429] comment: definition source Merck Index xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000019/ is_a: RXNO:0000332 ! aromatic substitution step created_by: batchelorc creation_date: 2014-03-03T09:00:00Z [Term] id: RXNO:0000494 name: Bartoli indole synthesis def: "Reaction of an ortho-substituted nitroarene with a vinyl Grignard reagent to yield a 7-substituted indole." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000019/ is_a: RXNO:0000395 ! indole synthesis relationship: RXNO:0000423 CHEBI:24828 ! has specified product indoles created_by: batchelorc creation_date: 2014-03-03T09:00:00Z [Term] id: RXNO:0000495 name: Barton olefination synonym: "Barton olefin synthesis" EXACT [] synonym: "Reaction of an aldehyde or ketone with a thioaldehyde or thioketone via a 1,3-4,thiadiazoline intermediate to yield an olefin." RELATED [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000023/ is_a: RXNO:0000479 ! olefination created_by: batchelorc creation_date: 2014-03-03T09:00:00Z [Term] id: RXNO:0000496 name: Barton-Zard reaction def: "Reaction of a nitroalkene with an alpha-isocyanoacetate to yield a substituted pyrrole." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000025/ is_a: RXNO:0000497 ! pyrrole synthesis relationship: RXNO:0000423 CHEBI:26455 ! has specified product pyrroles created_by: batchelorc creation_date: 2014-03-03T09:00:00Z [Term] id: RXNO:0000497 name: pyrrole synthesis def: "A reaction in which the intended product is a pyrrole that was not present in any of the reactants." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000347 ! azacycle synthesis intersection_of: MOP:0000543 ! molecular process intersection_of: RXNO:0000423 CHEBI:26455 ! has specified product pyrroles relationship: RXNO:0000423 CHEBI:26455 ! has specified product pyrroles created_by: batchelorc creation_date: 2014-03-03T09:00:00Z [Term] id: RXNO:0000498 name: Béchamp reduction def: "Reduction of an aromatic nitro compound to the corresponding arene by iron in some form in aqueous acid." [http://orcid.org/0000-0001-5985-7429] synonym: "Bechamp reduction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000028/ is_a: RXNO:0000037 ! functional group reduction relationship: RXNO:0000423 CHEBI:33860 ! has specified product aromatic amine created_by: batchelorc creation_date: 2014-03-03T09:00:00Z [Term] id: RXNO:0000499 name: Beirut reaction def: "Reaction of a benzofurazan 1-oxide with an enamine or enolate to yield a quinoxaline-1,4-dioxide." [http://orcid.org/0000-0001-5985-7429] comment: definition source Merck Index xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000030/ is_a: RXNO:0000108 ! ring expansion created_by: batchelorc creation_date: 2014-03-03T09:00:00Z [Term] id: RXNO:0000500 name: Bénary reaction def: "Reaction of a beta-aminovinylketone with a Grignard reagent to yield a substituted alpha,beta-unsaturated carbonyl compound." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000031/ is_a: RXNO:0000000 ! molecular skeleton joining reaction created_by: batchelorc creation_date: 2014-03-03T09:00:00Z [Term] id: RXNO:0000501 name: Feist-Bénary synthesis def: "Reaction of an alpha-haloketone or alpha-haloether with a 1,3-dicarbonyl compound in the presence of pyridine to yield a substituted furan." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000138/ is_a: RXNO:0000346 ! oxacycle synthesis relationship: BFO:0000057 CHEBI:16227 ! has_participant pyridine relationship: RXNO:0000423 CHEBI:24129 ! has specified product furans created_by: batchelorc creation_date: 2014-03-03T09:00:00Z [Term] id: RXNO:0000502 name: Boulton-Katritzky rearrangement def: "Rearrangement of a mancude eight-membered system containing a pentacycle into a different pentacycle where two of the ring atoms are ring atoms in the original molecule." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000202 ! ring rearrangement union_of: RXNO:0000503 ! monocyclic Boulton-Katritzky rearrangement union_of: RXNO:0000504 ! bicyclic Boulton-Katritzky rearrangement created_by: batchelorc creation_date: 2014-03-04T09:00:00Z [Term] id: RXNO:0000503 name: monocyclic Boulton-Katritzky rearrangement def: "Rearrangement of an azapentacycle containing a -N= system where there is an unsaturated three-heavy-atom substituent XYZ on the substituent double-bonded to the nitrogen, to a new azapentacycle where the pivotal nitrogen has broken its single bond and formed a new bond with atom Z." [doi:10.1039/j39670002005] is_a: RXNO:0000502 ! Boulton-Katritzky rearrangement created_by: batchelorc creation_date: 2014-03-04T09:00:00Z [Term] id: RXNO:0000504 name: bicyclic Boulton-Katritzky rearrangement def: "Rearrangement of a mancude bicyclo[4.3.0] compound with an unsaturated two-heavy-atom substituent on the six-membered ring alpha to the bridgehead to form a new mancude bicyclo[4.3.0] compound where the five-membered ring has been formed from the two-heavy-atom substituent and the original five-membered ring has been broken." [doi:10.1039/j29660001004] is_a: RXNO:0000502 ! Boulton-Katritzky rearrangement created_by: batchelorc creation_date: 2014-03-04T09:00:00Z [Term] id: RXNO:0000505 name: Mukaiyama-Hoshino method def: "Reaction of a primary nitro compound with phenyl isocynatate and triethylamine to yield a nitrile oxide." [http://orcid.org/0000-0001-5985-7429] xref: doi:10.1021/ja01505a017 is_a: RXNO:0000011 ! functional group modification created_by: batchelorc creation_date: 2014-03-04T09:00:00Z [Term] id: RXNO:0000506 name: Nef synthesis def: "Reaction of an aldehyde or ketone with a sodium acetylide to yield a propargyl alcohol." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000298/ is_a: RXNO:0000000 ! molecular skeleton joining reaction created_by: batchelorc creation_date: 2014-03-04T09:00:00Z [Term] id: RXNO:0000507 name: Krapcho decarboxylation def: "Reaction of an ester with an electron-withdrawing group alpha- to the ester functionality with a metal halide or pseudohalide to yield the shorter homologous system." [http://orcid.org/0000-0001-5985-7429] synonym: "Krapcho decarbalkoxylation" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000242/ is_a: MOP:0001713 ! decarboxylation is_a: RXNO:0000105 ! end-of-chain chain shortening created_by: batchelorc creation_date: 2014-03-04T09:00:00Z [Term] id: RXNO:0000508 name: Cadogan cyclization def: "Reaction of an aromatic nitro compound with an unsaturated substituent at the alpha-position to form a fused-ring nitrogen heterocycle." [http://orcid.org/0000-0001-5985-7429] synonym: "Cadogan reaction" EXACT [] synonym: "Cadogan ring closure" EXACT [] synonym: "Cadogan ring-closure" EXACT [] is_a: RXNO:0000052 ! fused-ring-system formation created_by: batchelorc creation_date: 2014-03-04T09:00:00Z [Term] id: RXNO:0000509 name: Cadogan indole synthesis def: "A Cadogan cyclization that results in an indole." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000395 ! indole synthesis is_a: RXNO:0000508 ! Cadogan cyclization intersection_of: RXNO:0000508 ! Cadogan cyclization intersection_of: RXNO:0000423 CHEBI:24828 ! has specified product indoles relationship: RXNO:0000423 CHEBI:24828 ! has specified product indoles created_by: batchelorc creation_date: 2014-03-05T09:00:00Z [Term] id: RXNO:0000510 name: Benkeser reduction def: "Addition of hydrogen atoms to unsaturated rings by means of alkali metals in low-molecular weight amines." [http://orcid.org/0000-0001-5985-7429] synonym: "Benkeser reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000032/ is_a: MOP:0000589 ! hydrogenation is_a: RXNO:0000041 ! addition reaction step created_by: batchelorc creation_date: 2014-03-06T09:00:00Z [Term] id: RXNO:0000511 name: Madelung indole synthesis def: "Reaction of an N-(2-alkylphenyl)alkanamide with strong base to form an indole." [http://orcid.org/0000-0001-5985-7429] synonym: "Madelung synthesis" EXACT [] xref: http://en.wikipedia.org/wiki/Madelung_synthesis xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000261/ is_a: MOP:0000628 ! molecular dehydration reaction is_a: RXNO:0000395 ! indole synthesis relationship: RXNO:0000423 CHEBI:24828 ! has specified product indoles created_by: batchelorc creation_date: 2014-03-07T09:00:00Z [Term] id: RXNO:0000512 name: Smith indole synthesis def: "Reaction of a N-(2-alkylphenyl)-trimethylsilylamine with two equivalents of organolithium and an ester or carboxylic acid to form an indole." [http://orcid.org/0000-0001-5985-7429] synonym: "Smith-modified Madelung synthesis" EXACT [] xref: http://en.wikipedia.org/wiki/Madelung_synthesis is_a: RXNO:0000395 ! indole synthesis relationship: RXNO:0000423 CHEBI:24828 ! has specified product indoles created_by: batchelorc creation_date: 2014-03-07T09:00:00Z [Term] id: RXNO:0000513 name: Mumm rearrangement def: "Rearrangement of an acyl imidate to form a carboximide." [http://orcid.org/0000-0001-5985-7429] xref: http://en.wikipedia.org/wiki/Mumm_rearrangement is_a: RXNO:0000025 ! rearrangement step relationship: RXNO:0000423 CHEBI:35636 ! has specified product carboximides created_by: batchelorc creation_date: 2014-03-07T09:00:00Z [Term] id: RXNO:0000514 name: Chapman rearrangement def: "Rearrangement of an aryl imino ether to yield an N,N-diaryl amide." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000074/ is_a: RXNO:0000025 ! rearrangement step created_by: batchelorc creation_date: 2014-03-07T09:00:00Z [Term] id: RXNO:0000515 name: Bergmann azlactone peptide synthesis def: "Reaction of an acetylated amino acid with an aldehyde then with a second amino acid, then hydrogenation and hydrolysis to form a dipeptide. It proceeds via an azlactone intermediate." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000038/ is_a: RXNO:0000000 ! molecular skeleton joining reaction created_by: batchelorc creation_date: 2014-03-10T09:00:00Z [Term] id: RXNO:0000516 name: Bergmann degradation def: "Removal of a terminal amino acid residue from a peptide by benzoylation, azidation, treatment with benzyl alcohol, hydrogenation and hydrolysis." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000039/ is_a: RXNO:0000517 ! terminal amino-acid residue cleaving reaction relationship: RXNO:0000423 CHEBI:37622 ! has specified product carboxamide relationship: RXNO:0000424 CHEBI:16670 ! has specified reactant peptide created_by: batchelorc creation_date: 2014-03-11T09:00:00Z [Term] id: RXNO:0000517 name: terminal amino-acid residue cleaving reaction def: "Removal of a terminal amino acid residue from a peptide." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000073 ! cleaving reaction relationship: RXNO:0000424 CHEBI:16670 ! has specified reactant peptide created_by: batchelorc creation_date: 2014-03-11T09:00:00Z [Term] id: RXNO:0000518 name: acridine synthesis def: "Ring formation reaction where the intended product is an acridine." [RSC:xp] is_a: RXNO:0000052 ! fused-ring-system formation is_a: RXNO:0000347 ! azacycle synthesis intersection_of: MOP:0000543 ! molecular process intersection_of: RXNO:0000423 CHEBI:22213 ! has specified product acridines relationship: RXNO:0000423 CHEBI:22213 ! has specified product acridines created_by: batchelorc creation_date: 2014-03-12T09:00:00Z [Term] id: RXNO:0000519 name: Bernthsen acridine synthesis def: "Reaction of a diarylamine in an organic acid or anhydride in the presence of zinc chloride to yield a 9-substituted acridine." [http://orcid.org/0000-0001-5985-7429] comment: Definition source Merck Index, modified for errors. synonym: "Bernthsen reaction" EXACT [] xref: doi:10.1039/b204243f xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000041/ is_a: RXNO:0000518 ! acridine synthesis relationship: RXNO:0000423 CHEBI:22213 ! has specified product acridines created_by: batchelorc creation_date: 2014-03-12T09:00:00Z [Term] id: RXNO:0000520 name: pyridine synthesis def: "Ring formation reaction where the intended product is a pyridine." [RSC:xp] is_a: RXNO:0000347 ! azacycle synthesis intersection_of: MOP:0000543 ! molecular process intersection_of: RXNO:0000423 CHEBI:26421 ! has specified product pyridines relationship: RXNO:0000423 CHEBI:26421 ! has specified product pyridines created_by: batchelorc creation_date: 2014-03-12T09:00:00Z [Term] id: RXNO:0000521 name: carbazole synthesis def: "Ring formation reaction where the intended product is a carbazole." [RSC:xp] is_a: RXNO:0000052 ! fused-ring-system formation is_a: RXNO:0000347 ! azacycle synthesis intersection_of: MOP:0000543 ! molecular process intersection_of: RXNO:0000423 CHEBI:48513 ! has specified product carbazoles relationship: RXNO:0000423 CHEBI:48513 ! has specified product carbazoles created_by: batchelorc creation_date: 2014-03-12T09:00:00Z [Term] id: RXNO:0000522 name: Betti reaction def: "Reaction of a phenol, an aromatic aldehyde and a primary aromatic or heterocyclic amine to yield a Betti's base, also known as an alpha-aminobenzylphenol." [http://orcid.org/0000-0001-5985-7429] synonym: "Betti synthesis" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000042/ is_a: RXNO:0000000 ! molecular skeleton joining reaction created_by: batchelorc creation_date: 2014-03-13T09:00:00Z [Term] id: RXNO:0000523 name: Bischler-Möhlau indole synthesis def: "Reaction of a terminal hydroxyketone or terminal halogenoketone with an aromatic amine to yield a 2-substituted indole." [http://orcid.org/0000-0001-5985-7429] comment: Originally this involved a solvent but this need not be the case, see for example doi:10.1039/b719641e synonym: "Bischler reaction" EXACT [] synonym: "Bischler-Mohlau indole synthesis" EXACT [] synonym: "Bischler-Mohlau reaction" EXACT [] synonym: "Bischler-Möhlau reaction" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000045/ is_a: RXNO:0000395 ! indole synthesis relationship: RXNO:0000423 CHEBI:24828 ! has specified product indoles relationship: RXNO:0000424 CHEBI:33860 created_by: batchelorc creation_date: 2014-03-13T09:00:00Z [Term] id: RXNO:0000524 name: Camps quinoline synthesis def: "Cyclisation of an o-acylaminoacetophenone in alcoholic sodium hydroxide to form a substituted hydroxyquinoline." [http://orcid.org/0000-0001-5985-7429] comment: The substituent on the amino nitrogen can affect the ratio of 1-hydroxy to 3-hydroxy products. synonym: "Camps cyclisation" EXACT [] synonym: "Camps cyclization" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000070/ is_a: RXNO:0000393 ! quinoline synthesis relationship: RXNO:0000423 CHEBI:26513 ! has specified product quinolines created_by: batchelorc creation_date: 2014-03-24T09:00:00Z [Term] id: RXNO:0000525 name: Castro-Stephens coupling def: "Palladium-catalysed coupling of copper(I) acetylides with aryl halides to yield arylacetylenes." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000073/ is_a: RXNO:0000000 ! molecular skeleton joining reaction is_a: RXNO:0000316 ! palladium-catalysed carbon-carbon coupling reaction relationship: RXNO:0000423 CHEBI:51929 ! has specified product arylacetylene relationship: RXNO:0000425 CHEBI:33363 ! has_catalyst palladium created_by: batchelorc creation_date: 2014-03-25T09:00:00Z [Term] id: RXNO:0000526 name: Chichibabin pyridine synthesis def: "Reaction of carbonyl compounds with ammonia or an amine to yield a pyridine." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000075/ is_a: RXNO:0000520 ! pyridine synthesis relationship: RXNO:0000423 CHEBI:26421 ! has specified product pyridines relationship: RXNO:0000424 CHEBI:36587 ! has specified reactant carbonyl compound created_by: batchelorc creation_date: 2014-03-25T09:00:00Z [Term] id: RXNO:0000527 name: Chichibabin reaction def: "Reaction of an azacycle with an alkali-metal amide to yield an aminated azacycle." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000076/ is_a: MOP:0000650 ! amination is_a: RXNO:0000331 ! substitution step created_by: batchelorc creation_date: 2014-03-25T09:00:00Z [Term] id: RXNO:0000528 name: Bodroux reaction def: "Reaction of a carboxylic ester with a magnesium iodide alkylamide to yield a carboxamide." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000052/ is_a: RXNO:0000011 ! functional group modification relationship: RXNO:0000424 CHEBI:33308 ! has specified reactant carboxylic ester created_by: batchelorc creation_date: 2014-03-27T09:00:00Z [Term] id: RXNO:0000529 name: Bogert-Cook synthesis def: "Condensation of beta-phenylethylmagnesium bromide with a cyclohexanone followed by cyclisation and dehydration in concentrated sulfuric acid to yield an octahydrophenanthrene." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000053/ is_a: RXNO:0000052 ! fused-ring-system formation created_by: batchelorc creation_date: 2014-03-27T09:00:00Z [Term] id: RXNO:0000530 name: Bohn-Schmidt reaction def: "Reaction of a hydroxylated anthraquinone with fuming sulfuric acid or sulfuric acid in boric acid in the presence of a mercury or selenium catalyst to form a more hydroxylated anthraquinone." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000054/ is_a: RXNO:0000373 ! functional group addition step created_by: batchelorc creation_date: 2014-03-27T09:00:00Z [Term] id: RXNO:0000531 name: Boord olefin synthesis def: "Etherification of an aldehyde followed by bromination and reaction with a Grignard reagent followed by treatment with zinc to eliminate the halogen and alkoxy groups to produce an olefin." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000055/ is_a: RXNO:0000479 ! olefination relationship: has_part MOP:0000656 ! elimination reaction relationship: has_part RXNO:0000014 ! Grignard reaction relationship: RXNO:0000424 CHEBI:17478 ! has specified reactant aldehyde created_by: batchelorc creation_date: 2014-03-27T09:00:00Z [Term] id: RXNO:0000532 name: Borsche-Drechsel cyclisation def: "Rearrangement of a cyclohexanone phenylhydrazone followed by oxidation to yield a carbazole." [http://orcid.org/0000-0001-5985-7429] synonym: "Borsche-Drechsel carbazole synthesis" EXACT [] synonym: "Borsche-Drechsel cyclization" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000056/ is_a: RXNO:0000521 ! carbazole synthesis relationship: RXNO:0000423 CHEBI:48513 ! has specified product carbazoles created_by: batchelorc creation_date: 2014-03-27T09:00:00Z [Term] id: RXNO:0000533 name: Bouveault aldehyde synthesis def: "Reaction of an organomagnesium or organolithium compound with an N,N'-disubstituted formamide to yield the next homologous aldehyde." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000057/ is_a: RXNO:0000070 ! chain lengthening relationship: RXNO:0000423 CHEBI:17478 ! has specified product aldehyde created_by: batchelorc creation_date: 2014-03-27T09:00:00Z [Term] id: RXNO:0000534 name: Bradsher cyclisation def: "Diels-Alder reaction of a dienophile with a cationic aromatic azadiene to yield a bridged-ring system." [http://orcid.org/0000-0001-5985-7429] synonym: "Bradsher cyclization" EXACT [] synonym: "Bradsher cycloaddition" EXACT [] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000060/ is_a: RXNO:0000052 ! fused-ring-system formation created_by: batchelorc creation_date: 2014-03-27T09:00:00Z [Term] id: RXNO:0000535 name: Bradsher reaction def: "Reaction of an ortho-acyldiarylmethane, catalysed by acid, to yield an anthracene." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000061/ is_a: RXNO:0000052 ! fused-ring-system formation created_by: batchelorc creation_date: 2014-04-08T09:00:00Z [Term] id: RXNO:0000536 name: Parham cyclisation def: "Reaction of a bromoarene that has an electrophilic group at the para-position with lithium bromide or lithium iodide followed by intramolecular cyclisation to yield a fused-ring system." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000317/ is_a: RXNO:0000052 ! fused-ring-system formation relationship: RXNO:0000424 CHEBI:37148 created_by: batchelorc creation_date: 2014-04-08T09:00:00Z [Term] id: CHEBI:37148 name: bromoarene is_a: CHEBI:50887 [Term] id: CHEBI:50887 name: haloarene is_a: CHEBI:36684 [Term] id: CHEBI:36684 name: organohalogen compound is_a: CHEBI:72695 [Term] id: RXNO:0000537 name: Quelet reaction def: "Reaction of an aliphatic aldehyde with a phenolic ether and hydrochloric acid to yield an alpha-chloroalkylphenolic ether." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000357/ is_a: RXNO:0000373 ! functional group addition step created_by: batchelorc creation_date: 2014-04-14T09:00:00Z [Term] id: RXNO:0000538 name: Chugaev reaction def: "Elimination of a water molecule from a secondary alcohol to yield an olefin." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000077/ is_a: RXNO:0000123 ! molecular skeleton elimination reaction relationship: RXNO:0000423 CHEBI:33641 ! has specified product olefin created_by: batchelorc creation_date: 2014-04-14T09:00:00Z [Term] id: RXNO:0000539 name: Cope elimination def: "Elimination of a hydroxylamine from an amine oxide by pyrolysis to yield an olefin." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/r85/ xref: https://en.wikipedia.org/wiki/Cope_reaction synonym: "Cope reaction" EXACT [] is_a: RXNO:0000123 ! molecular skeleton elimination reaction relationship: RXNO:0000423 CHEBI:33641 ! has specified product olefin created_by: batchelorc creation_date: 2014-04-14T09:00:00Z [Term] id: RXNO:0000540 name: Sugasawa reaction def: "Reaction of an aniline with a nitrile in the presence of boron trichloride and a Lewis acid to yield an ortho-acylated aniline." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000423/ is_a: RXNO:0000373 ! functional group addition step created_by: batchelorc creation_date: 2014-04-14T13:00:00Z [Term] id: RXNO:0000541 name: palladium-catalysed Kumada coupling def: "A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a palladium catalyst." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000144 ! Kumada coupling is_a: RXNO:0000316 ! palladium-catalysed carbon-carbon coupling reaction relationship: RXNO:0000425 CHEBI:33363 ! has_catalyst palladium created_by: batchelorc creation_date: 2014-04-14T13:00:00Z [Term] id: RXNO:0000542 name: nickel-catalysed Kumada coupling def: "A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a nickel catalyst." [http://orcid.org/0000-0001-5985-7429, http://orcid.org/0000-0002-4077-4719, RSC:db] is_a: RXNO:0000144 ! Kumada coupling relationship: RXNO:0000425 CHEBI:28112 ! has_catalyst nickel created_by: batchelorc creation_date: 2014-04-14T13:00:00Z [Term] id: RXNO:0000543 name: Eastwood reaction def: "Reaction of a 1,2-diol with triethoxymethane under heat to yield an olefin." [http://orcid.org/0000-0001-5985-7429] comment: The reaction is stereospecific. It proceeds via a 1,3-dioxolane intermediate. xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000121/ is_a: RXNO:0000123 ! molecular skeleton elimination reaction relationship: RXNO:0000423 CHEBI:33641 ! has specified product olefin created_by: batchelorc creation_date: 2014-04-15T11:00:00Z [Term] id: RXNO:0000544 name: Saegusa oxidation def: "Reaction of silyl enol ethers with palladium acetate in acetonitrile to yield an alpha,beta-unsaturated ketone." [doi:10.1021/jo00399a052] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000382/ is_a: RXNO:0000123 ! molecular skeleton elimination reaction created_by: batchelorc creation_date: 2014-04-22T16:00:00Z [Term] id: RXNO:0000545 name: Sandmeyer diphenylurea isatin synthesis def: "Reaction of diphenylthiourea with lead carbonate and potassium cyanide to form a cyanoformidine followed by ring closure and acid hydrolysis to yield isatin." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000384/ is_a: RXNO:0000395 ! indole synthesis relationship: RXNO:0000423 CHEBI:27539 ! has specified product isatin created_by: batchelorc creation_date: 2014-04-24T15:00:00Z [Term] id: RXNO:0000546 name: Sandmeyer isonitrosoacetanilide isatin synthesis def: "Reaction of aniline, hydroxylamine and chloral hydrate to form an aniline intermediate followed by cyclization in acid and hydrolysis to yield isatin." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000385/ is_a: RXNO:0000395 ! indole synthesis relationship: RXNO:0000423 CHEBI:27539 ! has specified product isatin created_by: batchelorc creation_date: 2014-04-24T15:00:00Z [Term] id: RXNO:0000547 name: Sarett oxidation def: "Oxidation of an alcohol with a pyridine-chromium trioxide complex to yield a carbonyl compound." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000387/ is_a: MOP:0000572 ! alcohol oxidation is_a: RXNO:0000012 ! functional group oxidation union_of: RXNO:0000548 ! Sarett primary alcohol oxidation union_of: RXNO:0000549 ! Sarett secondary alcohol oxidation relationship: RXNO:0000424 CHEBI:48420 ! has specified reactant chromium trioxide created_by: batchelorc creation_date: 2014-04-24T15:00:00Z [Term] id: RXNO:0000548 name: Sarett primary alcohol oxidation def: "Oxidation of a primary alcohol with a pyridine-chromium trioxide complex to yield an aldehyde." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000573 ! primary alcohol oxidation to aldehyde is_a: RXNO:0000547 ! Sarett oxidation created_by: batchelorc creation_date: 2014-04-24T15:00:00Z [Term] id: RXNO:0000549 name: Sarett secondary alcohol oxidation def: "Oxidation of a secondary alcohol with a pyridine-chromium trioxide complex to yield a ketone." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000574 ! secondary alcohol oxidation to ketone is_a: RXNO:0000547 ! Sarett oxidation created_by: batchelorc creation_date: 2014-04-24T15:00:00Z [Term] id: RXNO:0000550 name: Collins oxidation def: "Oxidation of a primary alcohol with a pyridine-chromium trioxide complex in dichloromethane to yield an aldehyde." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/rxn1500000387/ is_a: MOP:0000572 ! alcohol oxidation is_a: RXNO:0000012 ! functional group oxidation relationship: RXNO:0000424 CHEBI:48420 ! has specified reactant chromium trioxide created_by: batchelorc creation_date: 2014-04-24T15:00:00Z [Term] id: RXNO:0000551 name: reductive imination def: "A functional group modification where a carbonyl oxygen is replaced by an imine." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000555 ! imination is_a: RXNO:0000011 ! functional group modification [Term] id: RXNO:0000552 name: Leuckart aldehyde reaction def: "Reductive amination of an aldehyde with ammonium formate or formamide to form an amine." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000101 ! Leuckart reaction relationship: BFO:0000078 CHEBI:17478 ! has participant ceasing to exist aldehyde [Term] id: RXNO:0000553 name: Leuckart ketone reaction def: "Reductive amination of a ketone with ammonium formate or formamide to form an amine." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000101 ! Leuckart reaction relationship: BFO:0000078 CHEBI:17087 ! has participant ceasing to exist ketone [Term] id: RXNO:0000554 name: Appel bromination with tetrabromomethane def: "Conversion of an alcohol to an alkyl bromide with triphenylphosphine and tetrabromomethane." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000409 ! Appel bromination relationship: RXNO:0000424 CHEBI:47875 ! has specified reactant tetrabromomethane [Term] id: RXNO:0000555 name: Appel bromination with bromine def: "Conversion of an alcohol to an alkyl bromide with triphenylphosphine and bromine." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000409 ! Appel bromination relationship: RXNO:0000424 CHEBI:29224 ! has specified reactant dibromine [Term] id: RXNO:0000556 name: Corey-Fuchs terminal dibromoolefination def: "Reaction of an aldehyde with tetrabromomethane and triphenylphosphine to yield a terminal dibromoolefin." [http://orcid.org/0000-0001-5985-7429] comment: This is the first step of the Corey-Fuchs reaction. The second step is the Fritsch-Buttenberg-Wiechell rearrangement. synonym: "Corey-Fuchs reaction step 1" NARROW [] is_a: RXNO:0000479 ! olefination relationship: RXNO:0000424 CHEBI:36601 ! has specified reactant triphenylphosphane oxide relationship: RXNO:0000424 CHEBI:47875 ! has specified reactant tetrabromomethane !!! classes supplied by Roger [Term] id: RXNO:0000557 name: Heck-type reaction/cross-coupling comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000624 for Heck-type reaction and RXNO:0000603 for cross-coupling. is_obsolete: true [Term] id: RXNO:0000558 name: bromo Heck reaction/Liebeskind-Srogl coupling comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000625 for the bromo Heck reaction and RXNO:0000604 for Liebeskind-Srogl coupling. is_obsolete: true [Term] id: RXNO:0000559 name: chloro Heck reaction/Fukuyama coupling comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000626 for the chloro Heck reaction and RXNO:0000605 for Fukuyama coupling. is_obsolete: true [Term] id: RXNO:0000560 name: iodo Heck reaction/chloride Finkelstein reaction comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000627 for the iodo Heck reaction and RXNO:0000606 for the chloride Finkelstein reaction. is_obsolete: true [Term] id: RXNO:0000561 name: triflyloxy Heck reaction/bromide Finkelstein reaction comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000628 for the triflyloxy Heck reaction and RXNO:0000607 for the bromide Finkelstein reaction. is_obsolete: true [Term] id: RXNO:0000562 name: bromo Heck-type reaction/sulfonate ester Finkelstein reaction comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000629 for the bromo Heck-type reaction and RXNO:0000608 for the sulfonate ester Finkelstein reaction. is_obsolete: true [Term] id: RXNO:0000563 name: chloro Heck-type reaction/Sandmeyer fluorination comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000630 for the chloro Heck-type reaction and RXNO:0000609 for Sandmeyer fluorination. is_obsolete: true [Term] id: RXNO:0000564 name: acyclic Beckmann rearrangement/Sandmeyer chlorination comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000631 for acyclic Beckmann rearrangement and RXNO:0000610 for Sandmeyer chlorination. is_obsolete: true [Term] id: RXNO:0000565 name: Baeyer–Emmerling indole synthesis/Sandmeyer bromination comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000632 for Baeyer-Emmerling indole synthesis and RXNO:0000611 for Sandmeyer bromination. is_obsolete: true [Term] id: RXNO:0000566 name: bromo Sonogashira coupling/Sandmeyer iodination comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000633 for bromo Sonogashira coupling and RXNO:0000612 for Sandmeyer iodination. is_obsolete: true [Term] id: RXNO:0000567 name: bromo Suzuki coupling/iodo Heck reaction comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000634 for bromo Suzuki coupling and RXNO:0000613 for the iodo Heck reaction. is_obsolete: true [Term] id: RXNO:0000568 name: bromo Suzuki-type coupling/triflyloxy Heck reaction comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000635 for bromo Suzuki-type coupling and RXNO:0000628 for the triflyloxy Heck reaction. is_obsolete: true [Term] id: RXNO:0000569 name: bromolactonization/bromo Heck-type reaction comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000636 for bromolactonization and RXNO:0000629 for the bromo Heck-type reaction. is_obsolete: true [Term] id: RXNO:0000570 name: chloro Sonogashira coupling/chloro Heck-type reaction comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000637 for chloro Sonogashira coupling and RXNO:0000630 for the chloro Heck-type reaction. is_obsolete: true [Term] id: RXNO:0000571 name: chloro Suzuki coupling/Heck-type reaction comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000638 for chloro Suzuki coupling and RXNO:0000624 for the Heck-type reaction. is_obsolete: true [Term] id: RXNO:0000572 name: chloro Suzuki-type coupling/bromo Heck reaction comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000639 for chloro Suzuki-type coupling and RXNO:0000625 for the bromo Heck reaction. is_obsolete: true [Term] id: RXNO:0000573 name: chlorolactonization/chloro Heck reaction comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000640 for chlorolactonization and RXNO:0000626 for the chloro Heck reaction. is_obsolete: true [Term] id: RXNO:0000574 name: cyclic Beckmann rearrangement xref: NAMERXN:4.1.6 is_a: RXNO:0000026 ! Beckman rearrangement is_a: RXNO:0000347 ! azacycle synthesis !is_a: ??? ! name reaction [Term] id: RXNO:0000575 name: Dess-Martin aldehyde oxidation synonym: "aldehyde Dess-Martin oxidation" EXACT [] xref: NAMERXN:8.1.2 is_a: RXNO:0000256 ! Dess-Martin oxidation !is_a: ??? ! name reaction [Term] id: RXNO:0000576 name: Dess-Martin ketone oxidation synonym: "ketone Dess-Martin oxidation" EXACT [] xref: NAMERXN:8.1.3 is_a: RXNO:0000256 ! Dess-Martin oxidation !is_a: ??? ! name reaction [Term] id: RXNO:0000577 name: Friedlander quinoline synthesis synonym: "Friedländer synthesis" EXACT [] synonym: "Friedlander synthesis" EXACT [] synonym: "Friedlaender synthesis" EXACT [] xref: https://en.wikipedia.org/wiki/Friedländer_synthesis xref: NAMERXN:4.1.29 is_a: RXNO:0000393 ! quinoline synthesis !is_a: ??? ! name reaction [Term] id: RXNO:0000578 name: Gewald reaction def: "Reaction of an aldehyde or ketone with an alpha-cyanoester to form a 2-aminothiophene." [http://orcid.org/0000-0001-5985-7429] synonym: "Gewald thiophene synthesis" EXACT [] xref: https://en.wikipedia.org/wiki/Gewald_reaction xref: NAMERXN:4.3.4 is_a: RXNO:0000348 ! thiacycle synthesis [Term] id: RXNO:0000579 name: iodo Sonogashira coupling synonym: "Iodo Sonogashira coupling" EXACT [] xref: NAMERXN:3.3.4 is_a: RXNO:0000137 ! Sonogashira coupling [Term] id: RXNO:0000580 name: iodo Suzuki coupling synonym: "Iodo Suzuki coupling" EXACT [] synonym: "iodo Suzuki-Miyaura coupling" EXACT [] xref: NAMERXN:3.1.3 is_a: RXNO:0000140 ! Suzuki-Miyaura coupling is_a: RXNO:0000580 ! iodo Suzuki-type coupling [Term] id: RXNO:0000581 name: iodo Suzuki-type coupling synonym: "Iodo Suzuki-type coupling" EXACT [] synonym: "iodo Suzuki-Miyaura-type coupling" EXACT [] xref: NAMERXN:3.1.7 is_a: RXNO:0000592 ! Suzuki-type coupling [Term] id: RXNO:0000582 name: iodolactonization synonym: "iodolactonisation" EXACT [] xref: https://en.wikipedia.org/wiki/Iodolactonizaton xref: NAMERXN:4.2.15 is_a: RXNO:0000593 ! halolactonization [Term] id: RXNO:0000583 name: Niementowski quinazoline synthesis xref: https://en.wikipedia.org/wiki/Niementowski_quinazoline_synthesis xref: NAMERXN:4.1.30 is_a: RXNO:0000347 ! azacycle synthesis !is_a: ??? ! name reaction [Term] id: RXNO:0000584 name: Niementowski quinoline synthesis xref: https://en.wikipedia.org/wiki/Niementowski_quinoline_synthesis xref: NAMERXN:4.1.31 is_a: RXNO:0000393 ! quinoline synthesis !is_a: ??? ! name reaction [Term] id: RXNO:0000585 name: Pomeranz–Fritsch reaction synonym: "Pomeranz–Fritsch cyclization" EXACT [] synonym: "Pomeranz–Fritsch isoquinoline synthesis" EXACT [] xref: https://en.wikipedia.org/wiki/Pomeranz-Fritsch_reaction xref: NAMERXN:4.1.65 is_a: RXNO:0000347 ! azacycle synthesis !is_a: ??? ! name reaction [Term] id: RXNO:0000586 name: Steglich esterification xref: https://en.wikipedia.org/wiki/Steglich_esterification xref: NAMERXN:2.6.9 is_a: RXNO:0000360 ! O-acylation to ester -> esterification !is_a: ??? ! name reaction [Term] id: RXNO:0000587 name: triflyloxy Sonogashira coupling synonym: "Triflyloxy Sonogashira coupling" EXACT [] xref: NAMERXN:3.3.5 is_a: RXNO:0000137 ! Sonogashira coupling [Term] id: RXNO:0000588 name: triflyloxy Suzuki coupling synonym: "Triflyloxy Suzuki coupling" EXACT [] synonym: "triflyloxy Suzuki-Miyaura coupling" EXACT [] xref: NAMERXN:3.1.4 is_a: RXNO:0000140 ! Suzuki-Miyaura coupling is_a: RXNO:0000589 ! triflyloxy Suzuki-type coupling [Term] id: RXNO:0000589 name: triflyloxy Suzuki-type coupling synonym: "Triflyloxy Suzuki-type coupling" EXACT [] synonym: "triflyloxy Suzuki-Miyaura-type coupling" EXACT [] xref: NAMERXN:3.1.8 is_a: RXNO:0000592 ! Suzuki-type coupling [Term] id: RXNO:0000590 name: Wenker synthesis synonym: "Wenker aziridine synthesis" EXACT [] xref: https://en.wikipedia.org/wiki/Wenker_synthesis xref: NAMERXN:4.1.66 is_a: RXNO:0000347 ! azacycle synthesis !is_a: ??? ! name reaction [Term] id: RXNO:0000591 name: Hinsberg thiophene synthesis def: "Reaction of an alpha-diketone with a dialkyl thiodiacetate to form a thiophene dicarboxylic acid." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/r202/ xref: https://de.wikipedia.org/wiki/Hinsberg-Thiophensynthese is_a: RXNO:0000348 ! thiacycle synthesis [Term] id: RXNO:0000592 name: Suzuki-type coupling def: "The coupling of a boronic acid or boronic ester with an unsaturated halide, triflate or sulfonate." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000002 ! carbon-carbon coupling reaction [Term] id: RXNO:0000593 name: halolactonization def: "Addition of a carboxylic acid oxygen and halogen across a carbon-carbon double bond to form a lactone." [http://orcid.org/0000-0001-5985-7429] xref: https://en.wikipedia.org/wiki/Iodolactonization synonym: "halolactonisation" EXACT [] is_a: RXNO:0000346 [Term] id: RXNO:0000594 name: Ciamician-Dennstedt rearrangement def: "Expansion of a pyrrole ring by heating with a halogeno compond to form a 3-halogenopyridine." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000108 xref: https://www.rsc.org/Merck-Index/reaction/r78/ xref: https://es.wikipedia.org/wiki/Transposici%C3%B3n_de_Ciamician-Dennstedt [Term] id: RXNO:0000595 name: Claisen-Schmidt condensation def: "Condensation of an aromatic aldehyde with an aliphatic aldehyde or ketone in the presence of a relatively strong base to from an alpha,beta-unsaturated aldehyde or ketone." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/r81/ is_a: MOP:0000628 [Term] id: RXNO:0000596 name: Combes quinoline synthesis def: "Reaction of a beta-diketone with a primary arylamine to yield a quinoline. It is acid-catalysed." [http://orcid.org/0000-0001-5985-7429] xref: https://en.wikipedia.org/wiki/Combes_quinoline_synthesis xref: https://www.rsc.org/Merck-Index/reaction/r83/ is_a: RXNO:0000393 is_a: MOP:0000628 [Term] id: RXNO:0000596 name: Conrad-Limpach cyclisation def: "Reaction of an arylamine wtih a beta-ketoester to yield a 4-hydroxyquinoline." [http://orcid.org/0000-0001-5985-7429] synonym: "Conrad-Limpach synthesis" EXACT [] synonym: "Conrad-Limpach cyclization" EXACT [] xref: https://en.wikipedia.org/wiki/Conrad%E2%80%93Limpach_synthesis xref: https://www.rsc.org/Merck-Index/reaction/r84/ is_a: MOP:0000825 ! dealcoholative condensation reaction [Term] id: RXNO:0000597 name: Corey-Bakshi-Shibata reduction def: "Enantioselective reduction of a ketone to an alcohol with a chiral oxazaborolidine." [http://orcid.org/0000-0001-5985-7429] xref: https://www.rsc.org/Merck-Index/reaction/r87/ is_a: MOP:0000580 [Term] id: RXNO:0000598 name: Johnson-Corey-Chaykovsky reaction def: "Reaction of a sulfur ylide with a double-bond to produce a three-membered ring." [http://orcid.org/0000-0001-5985-7429] synonym: "Corey-Chaykovsky reaction" EXACT [] xref: https://en.wikipedia.org/wiki/Johnson%E2%80%93Corey%E2%80%93Chaykovsky_reaction xref: https://www.rsc.org/Merck-Index/reaction/r88/ is_a: RXNO:0000005 union_of: RXNO:0000599 union_of: RXNO:0000600 union_of: RXNO:0000601 union_of: RXNO:0000602 [Term] id: RXNO:0000599 name: Johnson-Corey-Chaykovsky epoxide synthesis def: "Reaction of a sulfur ylide with a ketone to produce an epoxide." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000346 [Term] id: RXNO:0000600 name: Johnson-Corey-Chaykovsky cyclopropane synthesis def: "Reaction of a sulfur ylide with an olefin to produce a cyclopropane." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000598 [Term] id: RXNO:0000601 name: Johnson-Corey-Chaykovsky aziridine synthesis def: "Reaction of a sulfur ylide with an imine to produce an aziridine." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000347 [Term] id: RXNO:0000602 name: Johnson-Corey-Chaykovsky thiirane synthesis def: "Reaction of a sulfur ylide with a thione to produce a thiirane." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000348 [Term] id: RXNO:0000603 name: cross-coupling def: "A joining reaction where a carbon-carbon bond is formed between unlike moieties." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000000 ! molecular skeleton joining reaction [Term] id: RXNO:0000604 name: Liebeskind-Srogl coupling def: "A cross-coupling reaction where a thioester and a boronic acid react to form a ketone. It uses a metal catalyst." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000603 ! cross-coupling [Term] id: RXNO:0000605 name: Fukuyama coupling def: "A cross-coupling reaction where a thioester and an organozinc halide react to form a ketone. It uses a palladium catalyst." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000603 ! cross-coupling [Term] id: RXNO:0000606 name: chloride Finkelstein reaction def: "The conversion of an alkyl chloride to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000155 ! Finkelstein reaction [Term] id: RXNO:0000607 name: bromide Finkelstein reaction def: "The conversion of an alkyl bromide to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000155 ! Finkelstein reaction [Term] id: RXNO:0000608 name: sulfonate ester Finkelstein reaction def: "The conversion of an alkyl sulfonate ester to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000155 ! Finkelstein reaction [Term] id: RXNO:0000609 name: Sandmeyer fluorination def: "An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) fluoride to form an aromatic fluoride." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000333 ! Sandmeyer halogenation [Term] id: RXNO:0000610 name: Sandmeyer chlorination def: "An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) chloride to form an aromatic chloride." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000333 ! Sandmeyer halogenation [Term] id: RXNO:0000611 name: Sandmeyer bromination def: "An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) bromide to form an aromatic bromide." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000333 ! Sandmeyer halogenation [Term] id: RXNO:0000612 name: Sandmeyer iodination def: "An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) iodide to form an aromatic iodide." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000333 ! Sandmeyer halogenation [Term] id: RXNO:0000613 name: imidazole synthesis def: "A planned reaction in which one of the products contains an imidazole system that was not in any of the reactants." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000347 [Term] id: RXNO:0000614 name: indazole synthesis def: "A planned reaction in which one of the products contains an indazole system that was not in any of the reactants." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000347 [Term] id: RXNO:0000615 name: piperazine synthesis def: "A planned reaction in which one of the products contains a piperazine system that was not in any of the reactants." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000347 [Term] id: RXNO:0000616 name: piperidine synthesis def: "A planned reaction in which one of the products contains a piperidine system that was not in any of the reactants." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000347 [Term] id: RXNO:0000617 name: pyrrolidine synthesis def: "A planned reaction in which one of the products contains a pyrrolidine system that was not in any of the reactants." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000347 [Term] id: RXNO:0000618 name: Hofmann-Löffler-Freytag reaction def: "An azacycle synthesis in which pyrrolidines or piperidines are formed by decomposition of protonated N-haloamines." [https://www.rsc.org/Merck-Index/reaction/r207/hofmann-löffler-freytag%20reaction] xref: https://www.rsc.org/Merck-Index/reaction/r207/ is_a: RXNO:0000347 union_of: RXNO:0000619 union_of: RXNO:0000620 [Term] id: RXNO:0000619 name: Hofmann-Löffler-Freytag piperidine synthesis def: "A Hofmann-Löffler-Freytag reaction in which the product is a piperidine." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000616 [Term] id: RXNO:0000620 name: Hofmann-Löffler-Freytag pyrrolidine synthesis def: "A Hofmann-Löffler-Freytag reaction in which the product is a pyrrolidine." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000617 [Term] id: RXNO:0000621 name: Hell-Volhard-Zelinsky reaction def: "An alpha-halogenation reaction where a carboxylic acid reacts with dibromine to form an alpha-bromocarboxylic acid." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000550 xref: https://www.rsc.org/Merck-Index/reaction/r194 relationship: RXNO:0000424 CHEBI:33575 relationship: RXNO:0000424 CHEBI:29224 relationship: RXNO:0000425 CHEBI:28659 [Term] id: CHEBI:28659 name: phosphorus atom is_a: CHEBI:33250 [Term] id: CHEBI:29224 name: dibromine is_a: CHEBI:23367 [Term] id: RXNO:0000622 name: Meerwein-Ponndorf-Verley reduction of an aldehyde def: "Meerwein-Ponndorf-Verley reduction of an aldehyde to the corresponding primary alcohol." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000037 is_a: RXNO:0000089 relationship: RXNO:0000424 CHEBI:17478 relationship: RXNO:0000423 CHEBI:15734 [Term] id: RXNO:0000623 name: Meerwein-Ponndorf-Verley reduction of a ketone def: "Meerwein-Ponndorf-Verley reduction of a ketone to the corresponding secondary alcohol." [http://orcid.org/0000-0001-5985-7429] is_a: RXNO:0000037 is_a: RXNO:0000089 relationship: RXNO:0000424 CHEBI:17087 relationship: RXNO:0000423 CHEBI:35681 [Term] id: RXNO:0000624 name: Heck-type reaction def: "A carbon-carbon coupling reaction where an organohalide or triflate couples to a terminal olefin to produce an internal olefin." [http://orcid.org/0000-0001-5985-7429, RSC:db] is_a: RXNO:0000002 [Term] id: RXNO:0000625 name: bromo Heck reaction def: "A Heck reaction where an organobromide couples to a terminal olefin to produce an internal olefin, catalysed by palladium." [http://orcid.org/0000-0001-5985-7429, RSC:db] is_a: RXNO:0000024 is_a: RXNO:0000629 is_obsolete: true [Term] id: RXNO:0000626 name: chloro Heck reaction def: "A Heck reaction where an organochloride couples to a terminal olefin to produce an internal olefin, catalysed by palladium." [http://orcid.org/0000-0001-5985-7429, RSC:db] is_a: RXNO:0000024 is_a: RXNO:0000630 [Term] id: RXNO:0000627 name: iodo Heck reaction def: "A Heck reaction where an organoiodide couples to a terminal olefin to produce an internal olefin, catalysed by palladium." [http://orcid.org/0000-0001-5985-7429, RSC:db] is_a: RXNO:0000024 [Term] id: RXNO:0000628 name: triflyloxy Heck reaction def: "A Heck reaction where an organotriflate couples to a terminal olefin to produce an internal olefin, catalysed by palladium." [http://orcid.org/0000-0001-5985-7429, RSC:db] is_a: RXNO:0000024 [Term] id: RXNO:0000629 name: bromo Heck-type reaction def: "A Heck-type reaction where an organobromide couples to a terminal olefin to produce an internal olefin." [http://orcid.org/0000-0001-5985-7429, RSC:db] is_a: RXNO:0000624 [Term] id: RXNO:0000630 name: chloro Heck-type reaction def: "A Heck-type reaction where an organochloride couples to a terminal olefin to produce an internal olefin." [http://orcid.org/0000-0001-5985-7429, RSC:db] is_a: RXNO:0000624 [Term] id: RXNO:0000631 name: acyclic Beckmann rearrangement xref: NAMERXN:2.8.1 is_a: RXNO:0000026 ! Beckman rearrangement !is_a: ??? ! name reaction [Term] id: RXNO:0000632 name: Baeyer–Emmerling indole synthesis xref: https://en.wikipedia.org/wiki/Baeyer-Emmerling_indole_synthesis xref: NAMERXN:4.1.41 is_a: RXNO:0000395 ! indole synthesis !is_a: ??? ! name reaction [Term] id: RXNO:0000633 name: bromo Sonogashira coupling synonym: "Bromo Sonogashira coupling" EXACT [] xref: NAMERXN:3.3.2 is_a: RXNO:0000137 ! Sonogashira coupling [Term] id: RXNO:0000634 name: bromo Suzuki coupling synonym: "Bromo Suzuki coupling" EXACT [] synonym: "bromo Suzuki-Miyaura coupling" EXACT [] xref: NAMERXN:3.1.1 is_a: RXNO:0000140 ! Suzuki-Miyaura coupling is_a: RXNO:0000635 ! bromo Suzuki-type coupling [Term] id: RXNO:0000635 name: bromo Suzuki-type coupling synonym: "Bromo Suzuki-type coupling" EXACT [] synonym: "bromo Suzuki-Miyaura-type coupling" EXACT [] xref: NAMERXN:3.1.5 is_a: RXNO:0000592 ! Suzuki-type coupling [Term] id: RXNO:0000636 name: bromolactonization synonym: "bromolactonisation" EXACT [] xref: NAMERXN:4.2.13 is_a: RXNO:0000593 ! halolactonization [Term] id: RXNO:0000637 name: chloro Sonogashira coupling synonym: "Chloro Sonogashira coupling" EXACT [] xref: NAMERXN:3.3.3 is_a: RXNO:0000137 ! Sonogashira coupling [Term] id: RXNO:0000638 name: chloro Suzuki coupling synonym: "Chloro Suzuki coupling" EXACT [] synonym: "chloro Suzuki-Miyaura coupling" EXACT [] xref: NAMERXN:3.1.2 is_a: RXNO:0000140 ! Suzuki-Miyaura coupling is_a: RXNO:0000639 ! chloro Suzuki-type coupling [Term] id: RXNO:0000639 name: chloro Suzuki-type coupling synonym: "Chloro Suzuki-type coupling" EXACT [] synonym: "chloro Suzuki-Miyaura-type coupling" EXACT [] xref: NAMERXN:3.1.6 is_a: RXNO:0000592 ! Suzuki-type coupling [Term] id: RXNO:0000640 name: chlorolactonization synonym: "chlorolactonisation" EXACT [] xref: NAMERXN:4.2.14 is_a: RXNO:0000593 ! halolactonization [Term] id: MOP:0000825 name: dealcoholative condensation def: "A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of an alcohol molecule." [http://orcid.org/0000-0001-5985-7429] is_a: MOP:0000627 [Term] id: MOP:0000826 name: dienophilicity def: "A disposition which is realised in a [4+2] reaction with a double-bonded system." [http://orcid.org/0000-0001-5985-7429] xref: http://goldbook.iupac.org/D01700.html is_a: BFO:0000016 [Typedef] id: BFO:0000055 name: realizes [Typedef] id: BFO:0000057 name: has_participant [Typedef] id: BFO:0000077 name: has participant beginning to exist is_a: BFO:0000057 ! has_participant [Typedef] id: BFO:0000078 name: has participant ceasing to exist is_a: BFO:0000057 ! has_participant [Typedef] id: BFO:0000162 name: has disposition at all times [Typedef] id: OBI:0000417 name: achieves_planned_objective def: "This relation obtains between a planned process and a objective specification when the criteria specified in the objective specification are met at the end of the planned process." [obi:AR, obi:BP, obi:PPPBbranch] domain: OBI:0000011 ! planned process range: IAO:0000005 ! objective specification [Typedef] id: RXNO:0000416 name: protects def: "The notion here is that a given reaction is meant to 'protect' a given group from reacting in a subsequent process and can be 'deprotected' later." [http://orcid.org/0000-0001-5985-7429] comment: can we chain 'has specified reactant' (RXNO:0000424) and has_part ? domain: RXNO:0000078 ! protection reaction range: CHEBI:24433 ! group is_a: BFO:0000078 ! has participant ceasing to exist [Typedef] id: RXNO:0000417 name: deprotects def: "If a reaction R deprotects a group G, then G is in the product where it wasn't in the reactant." [http://orcid.org/0000-0001-5985-7429] comment: can we chain 'has specified product' (RXNO:0000423) and has_part ? domain: RXNO:0000203 ! deprotection reaction range: CHEBI:24433 ! group is_a: BFO:0000077 ! has participant beginning to exist [Typedef] id: RXNO:0000423 name: has specified product comment: The difference between this and OBI's has_specified_output is that it is necessary that the participant starts to exist during the process. domain: RXNO:0000001 ! planned reaction step range: CHEBI:23367 ! molecular entity is_a: BFO:0000077 ! has participant beginning to exist [Typedef] id: RXNO:0000424 name: has specified reactant comment: The difference between this and OBI's has_specified_output is that it is necessary that the reactant ceases to exist during the process. domain: RXNO:0000001 ! planned reaction step range: CHEBI:23367 ! molecular entity is_a: BFO:0000078 ! has participant ceasing to exist [Typedef] id: RXNO:0000425 name: has_catalyst is_a: BFO:0000057 ! has_participant [Typedef] id: RXNO:0000469 name: has_intermediate is_a: BFO:0000057 ! has_participant [Typedef] id: has_part name: has_part [Typedef] id: part_of name: part_of