Journal of the American Chemical Society

The Halogenation of Diazomethane. Study of the Reactivities of Carbenes Derived from Halodiazomethanes1-3

GL Closs, JJ Coyle

Index: Closs,G.L.; Coyle,J.J. Journal of the American Chemical Society, 1965 , vol. 87, p. 4270 - 4279

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Citation Number: 71

Abstract

Halogenation qf diazomethane with less than molar amounts of t-butyl hypohalites at-100” gives halodiazomethanes in good yields. Thermolysis at-10 'and photol-vsis of chloro-and bromodiazomethane yield free halocarbenes with undergo insertion reactions and additions to olefins. Halocarbenes from halodiazomethanes are less reactive than methylene but more reactive than the chlorocarbenoid generated from methylene chloride by a-elimination. ...