The Stevens Rearrangement of Sulfur Ylide Generated by Electrochemical Reduction of Sulfonium Salt

Abstract

Abstract The cathodic reduction or a base treatment of a 1-cyanomethyltetrahydrothiophenonium salt gave the stabilized ylides which were conformed by the reaction with benzaldehyde. In the absence of benzaldehyde, the ring expanded product was obtained through the [1,2] Stevens rearrangement in good yield by both methods. The reaction mechanism was investigated by using B3LYP density functional calculations.