rsc-ontologies / rxno

Name Reaction Ontology
Creative Commons Attribution 4.0 International
39 stars 12 forks source link

Addition of 16 missing reactions to RXNO #33

Closed hujo91 closed 2 years ago

hujo91 commented 2 years ago

Addition of 16 reactions:

  1. Kabachnik-Fields reaction (RXNO:0000676) Def.: A three-component condensation reaction in which primary or secondary amines react with a carbonyl compound (aldehyde or ketone) and a dialkyl phosphonate (also called dialkyl phosphite) to form an alpha-aminophosphonate. Parent class: molecular skeleton joining reaction (RXNO:0000000) & molecular dehydration reaction (MOP:0000628)

  2. Baekeland-Manasse-Lederer reaction (RXNO:0000677) Def.: A polymerisation reaction in which phenol and formaldehyde react together in a chain reaction to form a phenol formaldehyde resin (also infrequently called phenoplast). Parent class: polymerisation reaction (RXNO:0000246)

  3. Aston-Greenburg rearrangement (RXNO:0000678) Def.: The rearrangement of an alpha-haloketone into an ester with a tertiary alpha-carbon atom by intramolecular migration of an alkyl or aryl group. Parent class: rearrangement step (RXNO:0000025)

  4. Baddeley isomerization (RXNO:0000679) Def.: The rearrangement/migration of alkyl groups in polyalkylbenzenes or polynuclear aromatic compounds in the presence of anhydrous aluminum chloride or the mixture of protonic acid and Lewis acid. Parent class: rearrangement step (RXNO:0000025)

  5. Fukuyama reduction (RXNO:0000680) Def.: The reduction of a thioester to an aldehyde by a silyl hydride in the presence of catalytic amounts of palladium. Parent class: functional group reduction (RXNO:0000037)

  6. Dötz reaction (RXNO:0000681) Def.: A three component cyclization of an aromatic or vinylic alkoxy pentacarbonyl chromium carbene complex, an alkyne and carbon monoxide to give a Cr(CO)3 coordinated phenol. Parent class: ring formation reaction step (RXNO:0000005) Synonym: Wulff-Dötz reaction

  7. Kulinkovich reaction (RXNO:0000682) Def.: The formation of a substituted cyclopropanol by reaction of a carboxylic ester with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst. A modified cyclopropanol product can be generated by addition of a terminal alkene as a further reactant. Parent class: ring formation reaction step (RXNO:0000005)

  8. Kulinkovich-de Meijere reaction (RXNO:0000683) Def.: The formation of a substituted cyclopropylamine by reaction of an amide with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst. Parent class: ring formation reaction step (RXNO:0000005)

  9. Kulinkovich-Szymoniak reaction (RXNO:0000684) Def.: The formation of a substituted primary cyclopropylamine by reaction of a nitrile with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst. Parent class: ring formation reaction step (RXNO:0000005)

  1. cyclotrimerization (RXNO:0000685) Def.: The formation of a trimer by cycloaddition of three unsaturated compounds (e.g. alkynes, alkenes, nitriles or mixtures of these). Usually, the reaction requires a metal catalyst. Parent class: ring formation reaction step (RXNO:0000005) & cycloaddition (MOP:0000562) => not added to RXNO because it fits better in the scope of MOP and will be added there, see #34
  1. Jacobsen epoxidation (RXNO:0000686) Def.: Chiral (salen)manganese(III)-catalyzed asymmetric epoxidation of alkenes. In addition to the catalyst, stoichiometric amounts of an oxidant (e.g. sodium hypochlorite) are required. Parent class: ring formation reaction step (RXNO:0000005) & epoxidation (MOP:0000671) Synonym: Jacobsen-Katsuki epoxidation

  2. Shi epoxidation (RXNO:0000687) Def.: Organocatalytic enantioselective epoxidation of trans- and tri-substituted olefins using a fructose derived chiral ketone catalyst and potassium peroxomonosulfate or H2O2 as an oxidant. Parent class: ring formation reaction step (RXNO:0000005) & epoxidation (MOP:0000671)

  3. Asinger reaction (RXNO:0000688) Def.: A multicomponent reaction (A-4CR) in which 3-thiazolines (2,5-dihydro-1,3-thiazoles) or mixtures of several 3-thiazolines are synthesized from elemental sulfur, an alpha-substitutable ketone or aldehyde, another carbonyl component and ammonia. Parent class: ring formation reaction step (RXNO:0000005) & thiacycle synthesis (RXNO:0000348) Synonym: Asinger thiazoline synthesis & Asinger-4 component reaction (A-4CR)

  4. haloform reaction (RXNO:0000689) Def.: Cleavage of methyl ketones (i.e. oxidative demethylation) with halogens (or hypohalites) in the presence of a base to give a carboxylic acid and haloform (trihalomethane). Parent class: end-of-chain chain shortening (RXNO:0000105) & halogenation (MOP:0000550) Synonym: Einhorn reaction & Lieben reaction

  5. Atherton-Todd reaction (RXNO:0000690) Def.: The conversion of dialkyl phosphites (dialkyl phosphonates) to dialkyl chlorophosphates using tetrachloromethane and a base (usually a primary, secondary or tertiary amine). Parent class: functional group oxidation (RXNO:0000012) & halogenation (MOP:0000550) Synonym: AT reaction

  6. Baeyer diarylmethane synthesis (RXNO:0000691) Def.: Synthesis of diarylmethane derivatives using an aldehyde and an aromatic compound at low temperature in an acidic medium. Parent class: molecular skeleton joining reaction (RXNO:0000000) & molecular dehydration reaction (MOP:0000628)

  7. silyl deprotection (RXNO:0000692) Def.: A hydroxyl group deprotection in which an silyl ether group is transformed into a hydroxy group. Parent class: hydroxy group deprotection (RXNO:0000430)

hujo91 commented 2 years ago

futher improvements & some more minor updates/additions:

batchelorc commented 2 years ago

Two things to add:

RXNO:0000676 - this is also a molecular dehydration reaction (MOP:0000628) RXNO:0000681 - probably useful to have "Wulff–Dötz reaction" as a synonym

hujo91 commented 2 years ago

Two things to add:

RXNO:0000676 - this is also a molecular dehydration reaction (MOP:0000628) RXNO:0000681 - probably useful to have "Wulff–Dötz reaction" as a synonym

@batchelorc thanks for the hints, I have taken them into account. One question regarding 10. cyclotrimerization (RXNO:0000685): Does the definition fit and does this reaction really belong in RXNO or would it not fit better in MOP due to its rather general character?

batchelorc commented 2 years ago

cyclotrimerization better for MOP, I think