title: Concurrent cyclopropanation by carbenes and carbanions.
abstract: The generation of phenylhalocarbenes in the presence of varying quantities of halide ions and electron-poor alkenes affords concurrent cyclopropanation of the alkenes by an equilibrating mixture of phenylhalocarbenes and phenylhalomethide carbanions, which permits the smooth modulation of selectivity between electron-poor alkenes and electron-rich alkenes, a feature of potential synthetic utility.
authors.affiliation: Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, New Brunswick, New Jersey 08903, USA. moss@rutchem.rutgers.edu
authors.forename: Robert A
authors.initials: RA
authors.lastname: Moss
authors.forename: Jingzhi
authors.initials: J
authors.lastname: Tian
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D000838:Anions / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis*; D006219:Halogens / Q000737:chemistry; D006838:Hydrocarbons; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000475:Alkenes; D000838:Anions; D003521:Cyclopropanes; D006219:Halogens; D006838:Hydrocarbons; C030011:carbene; D002244:Carbon; D008697:Methane