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- Carbene_C−H_insertion abstract "Carbene C−H insertion in organic chemistry concerns the insertion reaction of a carbene into a carbon–hydrogen bond. This organic reaction is of some importance in the synthesis of new organic compounds.Simple carbenes such as the methylene radical and dichlorocarbene are not regioselective towards insertion. When the carbene is stabilized by a metal the selectivity increases. The compound dirhodium tetraacetate is found to be especially effective. In a typical reaction ethyl diazoacetate (a well-known carbene precursor) and dirhodium tetraacetate react with hexane; the insertion into a C−H bond occurs 1% on one of the methyl groups, 63% on the alpha-methylene unit and 33% on the beta-methylene unit.The first such reaction was reported in 1981 by Teyssié In a general reaction mechanism for this reaction as proposed by Doyle in 1993 the metal that stabilizes the carbene, dissociates at the same time but not to the same degree as carbon–carbon bond formation and hydrogen atom migration. The reaction is distinct from a metal catalyzed C−H activation reaction where the metal actually inserts itself between carbon and hydrogen.Carbene carbon hydrogen insertionThe metal employed as a catalyst in this reaction historically was copper until superseded by rhodium. Other metals stabilize the carbene too much (e.g. molybdenum as in Fischer carbenes) or result in carbenes too reactive (e.g. gold, silver). Many dirhodium carboxylates and carboxamidates exist, including chiral ones. An effective chiral dirhodium catalyst is Rh2(MPPIM)4 with MPPIM (Methyl PhenylPropyl IMidazolidinecarboxylato) asymmetric ligand.Chiral dirhodium Catalysts, only one ligand displayed for clarityMost successful reactions are intramolecular within geometrically rigid systems, as pioneered by Wenkert (1982) and Taber (1982).We compared the use of different catalysts:Carbene carbon hydrogen insertion Wee 2000".
- Carbene_C−H_insertion thumbnail Carbene_carbon_hydrogen_insertion.svg?width=300.
- Carbene_C−H_insertion wikiPageID "24668006".
- Carbene_C−H_insertion wikiPageLength "4268".
- Carbene_C−H_insertion wikiPageOutDegree "31".
- Carbene_C−H_insertion wikiPageRevisionID "668909026".
- Carbene_C−H_insertion wikiPageWikiLink Asymmetric_ligand.
- Carbene_C−H_insertion wikiPageWikiLink Carbene.
- Carbene_C−H_insertion wikiPageWikiLink Carbon–carbon_bond.
- Carbene_C−H_insertion wikiPageWikiLink Carbon–hydrogen_bond.
- Carbene_C−H_insertion wikiPageWikiLink Carbon–hydrogen_bond_activation.
- Carbene_C−H_insertion wikiPageWikiLink Catalysis.
- Carbene_C−H_insertion wikiPageWikiLink Catalyst.
- Carbene_C−H_insertion wikiPageWikiLink Category:Carbenes.
- Carbene_C−H_insertion wikiPageWikiLink Category:Organic_reactions.
- Carbene_C−H_insertion wikiPageWikiLink Chiral_ligand.
- Carbene_C−H_insertion wikiPageWikiLink Chirality_(chemistry).
- Carbene_C−H_insertion wikiPageWikiLink Copper.
- Carbene_C−H_insertion wikiPageWikiLink C−H_activation_reaction.
- Carbene_C−H_insertion wikiPageWikiLink Dichlorocarbene.
- Carbene_C−H_insertion wikiPageWikiLink Dirhodium_tetraacetate.
- Carbene_C−H_insertion wikiPageWikiLink Ethyl_diazoacetate.
- Carbene_C−H_insertion wikiPageWikiLink Fischer_carbene.
- Carbene_C−H_insertion wikiPageWikiLink Gold.
- Carbene_C−H_insertion wikiPageWikiLink Hexane.
- Carbene_C−H_insertion wikiPageWikiLink Insertion_reaction.
- Carbene_C−H_insertion wikiPageWikiLink Intramolecular.
- Carbene_C−H_insertion wikiPageWikiLink Intramolecular_reaction.
- Carbene_C−H_insertion wikiPageWikiLink Methyl.
- Carbene_C−H_insertion wikiPageWikiLink Methyl_group.
- Carbene_C−H_insertion wikiPageWikiLink Methylene_(compound).
- Carbene_C−H_insertion wikiPageWikiLink Methylene_bridge.
- Carbene_C−H_insertion wikiPageWikiLink Methylene_radical.
- Carbene_C−H_insertion wikiPageWikiLink Molybdenum.
- Carbene_C−H_insertion wikiPageWikiLink Organic_chemistry.
- Carbene_C−H_insertion wikiPageWikiLink Organic_reaction.
- Carbene_C−H_insertion wikiPageWikiLink Reaction_mechanism.
- Carbene_C−H_insertion wikiPageWikiLink Regioselective.
- Carbene_C−H_insertion wikiPageWikiLink Regioselectivity.
- Carbene_C−H_insertion wikiPageWikiLink Rhodium.
- Carbene_C−H_insertion wikiPageWikiLink Rhodium(II)_acetate.
- Carbene_C−H_insertion wikiPageWikiLink Silver.
- Carbene_C−H_insertion wikiPageWikiLink Transition_metal_carbene_complex.
- Carbene_C−H_insertion wikiPageWikiLink File:Carbene_carbon_hydrogen_insertion.svg.
- Carbene_C−H_insertion wikiPageWikiLink File:Carbene_carbon_hydrogen_insertion_Wee_2000.svg.
- Carbene_C−H_insertion wikiPageWikiLink File:ChiraldirhodiumCatalysts.svg.
- Carbene_C−H_insertion wikiPageWikiLinkText "Carbene C−H insertion".
- Carbene_C−H_insertion wikiPageWikiLinkText "carbene insertion".
- Carbene_C−H_insertion hasPhotoCollection Carbene_C−H_insertion.
- Carbene_C−H_insertion wikiPageUsesTemplate Template:Reflist.
- Carbene_C−H_insertion subject Category:Carbenes.
- Carbene_C−H_insertion subject Category:Organic_reactions.
- Carbene_C−H_insertion comment "Carbene C−H insertion in organic chemistry concerns the insertion reaction of a carbene into a carbon–hydrogen bond. This organic reaction is of some importance in the synthesis of new organic compounds.Simple carbenes such as the methylene radical and dichlorocarbene are not regioselective towards insertion. When the carbene is stabilized by a metal the selectivity increases. The compound dirhodium tetraacetate is found to be especially effective.".
- Carbene_C−H_insertion label "Carbene C−H insertion".
- Carbene_C−H_insertion sameAs Inserción_de_carbeno.
- Carbene_C−H_insertion sameAs Insertion_de_carbène_dans_une_liaison_C-H.
- Carbene_C−H_insertion sameAs m.080jfd5.
- Carbene_C−H_insertion sameAs Q2379063.
- Carbene_C−H_insertion sameAs Q2379063.
- Carbene_C−H_insertion wasDerivedFrom Carbene_C−H_insertion?oldid=668909026.
- Carbene_C−H_insertion depiction Carbene_carbon_hydrogen_insertion.svg.
- Carbene_C−H_insertion isPrimaryTopicOf Carbene_C−H_insertion.