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- Rauhut–Currier_reaction abstract "The Rauhut–Currier reaction, also called the vinylogous Morita–Baylis–Hillman reaction, is an organic reaction describing (in its original scope) the dimerization or isomerization of electron-deficient alkenes such as enones by action of an organophosphine of the type R3P. In a more general description the RC reaction is any coupling of one active alkene / latent enolate to a second Michael acceptor, creating a new C–C bond between the alpha-position of one activated alkene and the beta-position of a second alkene under the influence of a nucleophilic catalyst. The reaction mechanism is essentially that of the related and better known Baylis–Hillman reaction (DABCO not phosphine, carbonyl not enone) but the Rauhut–Currier reaction actually predates it by several years. In comparison to the MBH reaction, the RC reaction lacks substrate reactivity and reaction selectivity. The original 1963 reaction described the dimerization of the ethyl acrylate to the ethyl diester of 2-methylene-glutaric acid with tributylphosphine in acetonitrile:This reaction was also found to work for acrylonitrile. RC cross-couplings are known but suffer from lack of selectivity. Amines such as DABCO can also act as catalyst. The reactivity is improved in intramolecular RC reactions, for example in the isomerization of di-enones to form cyclopentenes:A similar reaction by asymmetric synthesis organocatalyzed by a protected cysteine and potassium tert-butoxide afforded a cyclohexene with 95% enantiomeric excess:In this reaction the phosphine is replaced by the thiol group of cysteine but the reaction is the same.".
- Rauhut–Currier_reaction thumbnail Rauhut-Currier_reaction.png?width=300.
- Rauhut–Currier_reaction wikiPageID "9132444".
- Rauhut–Currier_reaction wikiPageLength "3592".
- Rauhut–Currier_reaction wikiPageOutDegree "38".
- Rauhut–Currier_reaction wikiPageRevisionID "673431561".
- Rauhut–Currier_reaction wikiPageWikiLink Acetonitrile.
- Rauhut–Currier_reaction wikiPageWikiLink Acrylonitrile.
- Rauhut–Currier_reaction wikiPageWikiLink Alkene.
- Rauhut–Currier_reaction wikiPageWikiLink Asymmetric_synthesis.
- Rauhut–Currier_reaction wikiPageWikiLink Baylis–Hillman_reaction.
- Rauhut–Currier_reaction wikiPageWikiLink Carbon–carbon_bond.
- Rauhut–Currier_reaction wikiPageWikiLink Catalysis.
- Rauhut–Currier_reaction wikiPageWikiLink Catalyst.
- Rauhut–Currier_reaction wikiPageWikiLink Category:Carbon-carbon_bond_forming_reactions.
- Rauhut–Currier_reaction wikiPageWikiLink Category:Name_reactions.
- Rauhut–Currier_reaction wikiPageWikiLink Cyclohexene.
- Rauhut–Currier_reaction wikiPageWikiLink Cyclopentene.
- Rauhut–Currier_reaction wikiPageWikiLink Cysteine.
- Rauhut–Currier_reaction wikiPageWikiLink C–C_bond.
- Rauhut–Currier_reaction wikiPageWikiLink DABCO.
- Rauhut–Currier_reaction wikiPageWikiLink Dimer_(chemistry).
- Rauhut–Currier_reaction wikiPageWikiLink Dimerization_(chemistry).
- Rauhut–Currier_reaction wikiPageWikiLink Enantiomeric_excess.
- Rauhut–Currier_reaction wikiPageWikiLink Enantioselective_synthesis.
- Rauhut–Currier_reaction wikiPageWikiLink Enol.
- Rauhut–Currier_reaction wikiPageWikiLink Enolate.
- Rauhut–Currier_reaction wikiPageWikiLink Enone.
- Rauhut–Currier_reaction wikiPageWikiLink Ethyl_acrylate.
- Rauhut–Currier_reaction wikiPageWikiLink Glutaric_acid.
- Rauhut–Currier_reaction wikiPageWikiLink Intramolecular.
- Rauhut–Currier_reaction wikiPageWikiLink Intramolecular_reaction.
- Rauhut–Currier_reaction wikiPageWikiLink Isomerization.
- Rauhut–Currier_reaction wikiPageWikiLink Methylene_group.
- Rauhut–Currier_reaction wikiPageWikiLink Michael_acceptor.
- Rauhut–Currier_reaction wikiPageWikiLink Michael_reaction.
- Rauhut–Currier_reaction wikiPageWikiLink Morita–Baylis–Hillman_reaction.
- Rauhut–Currier_reaction wikiPageWikiLink Nucleophile.
- Rauhut–Currier_reaction wikiPageWikiLink Nucleophilic.
- Rauhut–Currier_reaction wikiPageWikiLink Organic_reaction.
- Rauhut–Currier_reaction wikiPageWikiLink Organocatalysis.
- Rauhut–Currier_reaction wikiPageWikiLink Organophosphine.
- Rauhut–Currier_reaction wikiPageWikiLink Organophosphorus_compound.
- Rauhut–Currier_reaction wikiPageWikiLink Potassium_tert-butoxide.
- Rauhut–Currier_reaction wikiPageWikiLink Protecting_group.
- Rauhut–Currier_reaction wikiPageWikiLink Protective_group.
- Rauhut–Currier_reaction wikiPageWikiLink Reaction_mechanism.
- Rauhut–Currier_reaction wikiPageWikiLink Regioselectivity.
- Rauhut–Currier_reaction wikiPageWikiLink Thiol.
- Rauhut–Currier_reaction wikiPageWikiLink Tributylphosphine.
- Rauhut–Currier_reaction wikiPageWikiLink Vinylogous.
- Rauhut–Currier_reaction wikiPageWikiLink Vinylogy.
- Rauhut–Currier_reaction wikiPageWikiLink File:Rauhut-Currier-enantioselective.png.
- Rauhut–Currier_reaction wikiPageWikiLink File:Rauhut-Currier-intramolecular.png.
- Rauhut–Currier_reaction wikiPageWikiLink File:Rauhut-Currier_reaction.png.
- Rauhut–Currier_reaction wikiPageWikiLinkText "Rauhut–Currier reaction".
- Rauhut–Currier_reaction hasPhotoCollection Rauhut–Currier_reaction.
- Rauhut–Currier_reaction wikiPageUsesTemplate Template:Reflist.
- Rauhut–Currier_reaction wikiPageUsesTemplate Template:Use_dmy_dates.
- Rauhut–Currier_reaction subject Category:Carbon-carbon_bond_forming_reactions.
- Rauhut–Currier_reaction subject Category:Name_reactions.
- Rauhut–Currier_reaction comment "The Rauhut–Currier reaction, also called the vinylogous Morita–Baylis–Hillman reaction, is an organic reaction describing (in its original scope) the dimerization or isomerization of electron-deficient alkenes such as enones by action of an organophosphine of the type R3P.".
- Rauhut–Currier_reaction label "Rauhut–Currier reaction".
- Rauhut–Currier_reaction sameAs Reação_de_Rauhut-Currier.
- Rauhut–Currier_reaction sameAs m.027ywcd.
- Rauhut–Currier_reaction sameAs Q7296135.
- Rauhut–Currier_reaction sameAs Q7296135.
- Rauhut–Currier_reaction wasDerivedFrom Rauhut–Currier_reaction?oldid=673431561.
- Rauhut–Currier_reaction depiction Rauhut-Currier_reaction.png.
- Rauhut–Currier_reaction isPrimaryTopicOf Rauhut–Currier_reaction.