Ortho-bis (alkylsulphonyl) benzenes: The fate of their electrochemically formed anion radical: SN2 vs cleavage reaction

Article abstract of DOI:10.1016/S0040-4039(00)74360-7

Title compounds are electrochemically reduced into anion radicals of rather long lifetime. Surprisingly decomposition of such intermediates does not correspond as expected to a pure sulphur-carbon bond cleavage but mainly to a nucleophilic substitution toward the substrate. Nevertheless, cleavage reactions are observed in the case of methyl compounds.