The Elimination Reaction of Vicinal Disulphonyloxy Compounds with Sodium Iodide

Abstract

The elimination of two tosyloxy groups from vicinal ditosyloxy compounds by reaction with sodium iodide has been investigated. The reaction involves nucleophilic displacement of one tosyloxy group ; this is followed by the simultaneous elimination of the second tosyloxy group and iodine, if the steric arrangement is favourable; if it is unfavourable, a second displacement by an iodide ion probably occurs to give substituents having a trans-arrangement suitable for elimination. In one case, that of the ditosyl derivative of trans-cyclohexane-1,2-diol, the intermediate cis-2-iodocyclohexyl toluene-p-sulphonate was isolated.