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Solvolysis of 1-arylethyl(dimethyl)sulphonium ions and a reassessment of proposed SN2C+ character in solvolyses of 1-arylethyl systems

The specific rates of solvolysis of three 1-arylethyl(dimethyl) sulphonium ions, with substituent σ + values of ≤0.15, are found to be essentially solvent independent, consistent with the absence of any nucleophilic participation by solvent in the rate-determining step; a reassessment of rate data for 1-arylethyl toluene-p-sulphonates containing more electron-withdrawing substituents (σ + >0.4) suggests that the data, now indicating nucleophilic assistance, are better accommodated by the incursion of conventional S N 2 character, rather than the proposed rate-determining attack on a preformed ion pair