Electrophilic additions to alkenes, part V. Substituent effects on the rates of reaction of arylsulphenyl chlorides with cyclohexene

C Brown, DR Hogg

Index: Brown,C.; Hogg,D.R. Journal of the Chemical Society [Section] B: Physical Organic, 1968 , p. 1262 - 1265

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Citation Number: 8

Abstract

The rates of addition of a series of 4-substituted 2-nitrobenzenesulphenyl chlorides to cyclohexene in acetic acid solution increase with increasing electron-release from the 4- substituent, and a value of–0· 715 is obtained for the reaction constant, ρ+, at 25°. The ρ+ correlation is in agreement with the mechanism proposed for this reaction, which postulates an episulphonium ion rather than an open carbonium ion as the cationic intermediate. The ...