The acid-catalysed hydrolysis of episulphoxides

Abstract

The acid-catalysed hydrolyses of a number of episulphoxides in aqueous mineral acids have been studied. Ethylene, propylene, and styrene episulphoxides hydrolyse by concurrent A-2 and nucleophile-catalysed pathways. 3-Methyl- and 3,3-dimethyl-butylene 1,2-episulphoxide hydrolyse in sulphuric acid by an A-2 mechanism but in concentrated perchloric acid their rate profiles pass through a maximum and there is a changeover from an A-2 to an A-1 mechanism. Values of pK_BH⁺ for these two episulphoxides have been determined.