The Journal of Organic Chemistry

Substituent effects in the homolytic brominolysis of substituted phenylcyclopropanes

DE Applequist, LF McKenzie

Index: Applequist,D.E.; McKenzie,L.F. Journal of Organic Chemistry, 1976 , vol. 41, p. 2262 - 2266

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Citation Number: 12

Abstract

Competitive photochemical brominolyses of substituted phenylcyclopropanes in carbon disulfide at 20" C gave linear Hammett plots with CT+(p=-1.84, correlation coefficient-0.996) or with u (p=-2.16, correlation coefficient-0.982). The substituent effect is similar to that found in homolytic bromination of toluenes, and is similarly interpreted in terms of a polar transition state for the displacement reaction.