Concurrent solvolytic and non-solvolytic reactions of benzyl azoxytoluene-p-sulphonate in aqueous trifluoroethanol containing bases: an unprecedented mechanistic …

H Maskill

Index: Maskill, H. Journal of the Chemical Society, Chemical Communications, 1986 , p. 1433 - 1435

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Citation Number: 3

Abstract

Benzyl azoxytoluene-p-sulphonate (1) undergoes heterolytic fragmentation on solvolysis with the anticipated electron flow from benzyl towards the toluene-p-sulphonate leaving group, but suffers concurrent nucleophilic attack by basic solutes at the sulphur atom of the toluene-p-sulphonate moiety with consequent heterolysis and electron flow in the opposite sense, the benzylazoxy group now being the nucleofuge.

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