The nucleophilic character of N-halogenosulphonamide ion

Abstract

N-Chloro-N-sodiobenzenesulphonamides react with ethylene oxide in aqueous solution to give the corresponding N-chloro-N-(2-hydroxyethyl)sulphonamides. The reaction has been shown to involve a nucleophilic attack by N-chlorosulphonamide ion on the epoxide; the nucleophilicity of this ion is comparable to that of azide. N-Bromobenzenesulphonamide behaves similarly but the instability of the product precludes an accurate assessment of the effect in this case. Two further examples of nucleophilic displacement by N-chloro-N-sodiosulphonamides are described: the reaction of both aromatic and aliphatic derivatives with propanesultone in water and the reaction of the aliphatic species with ethylene sulphate in acetone.