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Nucleophilic character of an electrophilic carbene. Synthesis of cyclopropanes by thermal decomposition of 3-chloro-3-phenyldiazirine

✍ Scribed by Michael P. Doyle; Jan W. Terpstra; Charles H. Winter

Book ID: 104232504
Publisher: Elsevier Science
Year: 1984
Tongue: French
Weight: 238 KB
Volume: 25
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)80057-5

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✦ Synopsis

Chlorophenylcarbene reacts with electrophilic olefins to form cyclopropane products in high yield through proposed ylide intermediates. Diazirines, cyclic structural isomers of diazo compounds, are routinely employed as carbene precursors. 1 Although photolytic methods are most commonly used for dinitrogen extrusion,1'2 thermal decomposition of diazirines also provides entry to carbenes. ly3 The specific characteristics of carbenes generated from diazirines and other carbenic sources are subjects of intense current interest 4 and, recently, the spectrum of carbene philicity

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