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J Am Chem Soc. 2005 Jun 29;127(25):8960-1.

Concurrent cyclopropanation by carbenes and carbanions.

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1
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, New Brunswick, New Jersey 08903, USA. moss@rutchem.rutgers.edu

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.

PMID:
15969567
DOI:
10.1021/ja052426p
[Indexed for MEDLINE]
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