Only a concerted (E2) mechanism is possible for the formation of phenyl sulphene in alkali from toluene-α-sulphonate esters of phenois with pKa < 6 because the corresponding anions are estimated to have half-lives less than the vibration time of an S–O Ar bond and hence do not exist as identifiable species.
K. T. Douglas, A. Steltner and A. Williams, J. Chem. Soc., Chem. Commun., 1975, 353 DOI: 10.1039/C39750000353
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