title: α-Diazo-β-ketonitriles: uniquely reactive substrates for arene and alkene cyclopropanation.
abstract: An investigation of the intramolecular cyclopropanation reactions of α-diazo-β-ketonitriles is reported. These studies reveal that α-diazo-β-ketonitriles exhibit unique reactivity in their ability to undergo arene cyclopropanation reactions; other similar acceptor-acceptor-substituted diazo substrates instead produce mixtures of C-H insertion and dimerization products. α-Diazo-β-ketonitriles also undergo highly efficient intramolecular cyclopropanation of tri- and tetrasubstituted alkenes. In addition, the α-cyano-α-ketocyclopropane products are demonstrated to serve as substrates for SN2, SN2', and aldehyde cycloaddition reactions.
authors: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
authors: Roger R
authors: RR
authors: Nani
authors: Sarah E
authors: SE
authors: Reisman
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D003979:Diazonium Compounds / Q000737:chemistry*; D019281:Dimerization; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*
chemical_list: D000475:Alkenes; D003521:Cyclopropanes; D003979:Diazonium Compounds; D006841:Hydrocarbons, Aromatic; D009570:Nitriles