Solvolysis of 2-adamantyl ONN-azoxytoluene-p-sulphonate. A new reaction

Abstract

The first secondary alkyl azoxyarenesulphonate, 2-adamantyl azoxytosylate, has been made and shown to have the Z configuration about the nitrogen–nitrogen double bond; rates of solvolysis and activation parameters in aqueous ethanol, aqueous trifluoroethanol, and aqueous hexafluoropropan-2-ol have been determined and a solvolytic mechanism involving unimolecular fragmentation and carbonium ion intermediates is proposed.