Nucleophilic substitution at sulphur. Part 2. The acid-catalysed hydrolysis of arenesulphinamides

Abstract

The acid-catalysed hydrolyses of some bis-(para-substituted phenyl)benzenesulphinamides have been studied in aqueous solutions of perchloric acid and the substituent effects analysed. The kinetics of hydrolysis of p-tolyl-toluene-p-sulphinamide in a number of mineral acids have been studied in some detail. The hydrolysis at 25 °C proceeds by both an acid catalysed (A-2) and a hydrogen ion-dependent nucleophile-catalysed reaction. At higher temperatures hydrogen ion-independent nucleophilic catalysis can also be identified