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- Stetter_reaction abstract "The Stetter reaction is a reaction used in organic chemistry to form carbon-carbon bonds through a 1,4-addition reaction utilizing a nucleophilic catalyst. While the related 1,2-addition reaction, the benzoin condensation, was known since the 1830s, the Stetter reaction was not reported until 1973 by Dr. Hermann Stetter. The reaction provides synthetically useful 1,4-dicarbonyl compounds and related derivatives from aldehydes and Michael acceptors. Unlike 1,3-dicarbonyls, which are easily accessed through the Claisen condensation, or 1,5-dicarbonyls, which are commonly made using a Michael reaction, 1,4-dicarbonyls are challenging substrates to synthesize, yet are valuable starting materials for several organic transformations, including the Paal–Knorr synthesis of furans and pyrroles. Traditionally utilized catalysts for the Stetter reaction are thiazolium salts and cyanide anion, but more recent work toward the asymmetric Stetter reaction has found triazolium salts to be effective. The Stetter reaction is an example of umpolung chemistry, as the inherent polarity of the aldehyde is reversed by the addition of the catalyst to the aldehyde, rendering the carbon center nucleophilic rather than electrophilic.".
- Stetter_reaction thumbnail Stetter_reaction_general_example.png?width=300.
- Stetter_reaction wikiPageID "4436559".
- Stetter_reaction wikiPageLength "19621".
- Stetter_reaction wikiPageOutDegree "57".
- Stetter_reaction wikiPageRevisionID "646836073".
- Stetter_reaction wikiPageWikiLink Addition_reaction.
- Stetter_reaction wikiPageWikiLink Allylic_strain.
- Stetter_reaction wikiPageWikiLink Baylis–Hillman_reaction.
- Stetter_reaction wikiPageWikiLink Benzoin_condensation.
- Stetter_reaction wikiPageWikiLink Brook_rearrangement.
- Stetter_reaction wikiPageWikiLink Carbene.
- Stetter_reaction wikiPageWikiLink Carbon–carbon_bond.
- Stetter_reaction wikiPageWikiLink Catalysis.
- Stetter_reaction wikiPageWikiLink Category:Addition_reactions.
- Stetter_reaction wikiPageWikiLink Category:Carbon-carbon_bond_forming_reactions.
- Stetter_reaction wikiPageWikiLink Category:Name_reactions.
- Stetter_reaction wikiPageWikiLink Claisen_condensation.
- Stetter_reaction wikiPageWikiLink Diastereomer.
- Stetter_reaction wikiPageWikiLink Electrophile.
- Stetter_reaction wikiPageWikiLink Enantioselective_synthesis.
- Stetter_reaction wikiPageWikiLink Michael_reaction.
- Stetter_reaction wikiPageWikiLink Nitroalkene.
- Stetter_reaction wikiPageWikiLink Nucleophile.
- Stetter_reaction wikiPageWikiLink Nucleophilic_conjugate_addition.
- Stetter_reaction wikiPageWikiLink Organic_chemistry.
- Stetter_reaction wikiPageWikiLink Organic_synthesis.
- Stetter_reaction wikiPageWikiLink Paal–Knorr_synthesis.
- Stetter_reaction wikiPageWikiLink Resonance_(chemistry).
- Stetter_reaction wikiPageWikiLink Ring-closing_metathesis.
- Stetter_reaction wikiPageWikiLink Ronald_Breslow.
- Stetter_reaction wikiPageWikiLink Stereoelectronics.
- Stetter_reaction wikiPageWikiLink Synthon.
- Stetter_reaction wikiPageWikiLink Thiamine.
- Stetter_reaction wikiPageWikiLink Umpolung.
- Stetter_reaction wikiPageWikiLink Ylide.
- Stetter_reaction wikiPageWikiLink File:2-aminofurans_from_Stetter_chemistry.png.
- Stetter_reaction wikiPageWikiLink File:3-aminofurans_from_Stetter_chemistry.png.
- Stetter_reaction wikiPageWikiLink File:Amino_acid_synthesis_with_Stetter_reaction.png.
- Stetter_reaction wikiPageWikiLink File:Asymmetric_Intermolecular_Stetter_Reactions.png.
- Stetter_reaction wikiPageWikiLink File:Asymmetric_Stetter_Reaction_with_Nitroalkenes.png.
- Stetter_reaction wikiPageWikiLink File:Breslow_intermediate_formation.png.
- Stetter_reaction wikiPageWikiLink File:Coupling_Isomerization_Stetter_Paal_Knorr.png.
- Stetter_reaction wikiPageWikiLink File:First_Asymmetric_Stetter_Reactions.png.
- Stetter_reaction wikiPageWikiLink File:Hirsutic_acid_c.png.
- Stetter_reaction wikiPageWikiLink File:Quaternary_Center_Formation.png.
- Stetter_reaction wikiPageWikiLink File:Reaction_scheme_of_cyclic_diketone_stetter_reaction.png.
- Stetter_reaction wikiPageWikiLink File:Roseophilin_synthesis.png.
- Stetter_reaction wikiPageWikiLink File:Scope_of_Stetter_Reaction.png.
- Stetter_reaction wikiPageWikiLink File:Silastetter_Reaction.png.
- Stetter_reaction wikiPageWikiLink File:Stetter_reaction_general_example.png.
- Stetter_reaction wikiPageWikiLink File:Stetter_reaction_mechanism.png.
- Stetter_reaction wikiPageWikiLink File:Stetter_reaction_with_acyclic_diketones.png.
- Stetter_reaction wikiPageWikiLink File:Stetter_reaction_with_acylimines.png.
- Stetter_reaction wikiPageWikiLinkText "Stetter reaction".
- Stetter_reaction wikiPageUsesTemplate Template:Reflist.
- Stetter_reaction subject Category:Addition_reactions.
- Stetter_reaction subject Category:Carbon-carbon_bond_forming_reactions.
- Stetter_reaction subject Category:Name_reactions.
- Stetter_reaction hypernym Reaction.
- Stetter_reaction type Disease.
- Stetter_reaction type Eponym.
- Stetter_reaction type Reaction.
- Stetter_reaction comment "The Stetter reaction is a reaction used in organic chemistry to form carbon-carbon bonds through a 1,4-addition reaction utilizing a nucleophilic catalyst. While the related 1,2-addition reaction, the benzoin condensation, was known since the 1830s, the Stetter reaction was not reported until 1973 by Dr. Hermann Stetter. The reaction provides synthetically useful 1,4-dicarbonyl compounds and related derivatives from aldehydes and Michael acceptors.".
- Stetter_reaction label "Stetter reaction".
- Stetter_reaction sameAs Q904710.
- Stetter_reaction sameAs Stetter-Reaktion.
- Stetter_reaction sameAs m.0c298w.
- Stetter_reaction sameAs Q904710.
- Stetter_reaction sameAs Stetter反应.
- Stetter_reaction wasDerivedFrom Stetter_reaction?oldid=646836073.
- Stetter_reaction depiction Stetter_reaction_general_example.png.
- Stetter_reaction isPrimaryTopicOf Stetter_reaction.