Concurrent cyclopropanation by carbenes and carbanions.
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.
Moss
Robert A
RA
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, New Brunswick, New Jersey 08903, USA. moss@rutchem.rutgers.edu
Tian
Jingzhi
J
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
D000475:Alkenes; D000838:Anions; D003521:Cyclopropanes; D006219:Halogens; D006838:Hydrocarbons; C030011:carbene; D002244:Carbon; D008697:Methane