Interaction of benzenedisulphonyl chlorides, aluminium chloride, and benzene

Abstract

In conditions where benzenesulphonyl chloride, aromatic hydrocarbons, and aluminium chloride provide diaryl sulphones as the only organic products, the three phenylsulphonylbenzenesulphonyl chlorides give products both of sulphonylation, in the order m- > p- > o-, and of reduction to the sulphinic acid, with concomitant formation of chlorobenzene, in the order o- > p- > m-. The three benzenedisulphonyl chlorides provide products of sulphonylation, in the order m- > p- > o-, but reduction takes place in the order o- > m- > p-. The mechanism of the reactions is discussed.