Internal return in the solvolysis of secondary alkyl arenesulphonates

Abstract

In highly ionizing solvolytic media, such as hexafluoropropan-2-ol, 2-adamantyl azoxytoluene-p-sulphonate gives only solvent-derived products, while in a solvent less conducive to carbonium ions such as ethanol, 2-admantyl toluene-p-sulphonate may be detected among the solvolysis products; this demonstrates that the 2-admantyl toluene-p-sulphonate may be detected among the solvolysis products; this demonstrates that the 2-adamantyl cation may be captured by the very weakly nucleophilic toluene-p-sulphonate anion even in a strongly nucleophilic medium and, with other results, establishes that internal return accompanies the solvolysis of 2-adamantyl toluene-p-sulphonate.