Sulphuryl chloride as an electrophile. Part III. Reactions with alkylbenzenes in nitromethane

Abstract

The rates of reaction of a number of alkylbenzenes with sulphuryl chloride in nitromethane have been studied. Substitution occurs predominantly in the benzene ring at 25°; the principal electrophile is molecular sulphuryl chloride, although molecular chlorine, formed by the pre-equilibrium, SO₂Cl₂⇌ SO₂+ Cl₂, also contributes to some extent. The mechanism of the heterolytic reaction appears to be similar to those of the corresponding reactions of the molecular halogens; the attack by the reagent upon the hydrocarbon is the rate-determining stage.