Generation of Selenonium Ylides from Selenonium Salts by Electrochemical Reduction and their Reactions

The cathodic reduction of selenonium salts bearing substituted benzyl, allyl and ethoxycarbonylmethyl group gave the ylides which were confirmed by the Corey-Chaykovsky reaction with benzaldehyde. In the absence of benzaldehyde, the [2,3] Sigmatropic rearrangement, coupling reaction, and olefin or cyclopropane formation via the ylides occurred in good yield. To elucidate the reaction mechanisms of the reactions of selenium ylides from selenium salts bearing allyl group, the theoretical density functional calculations were performed by using B3LYP with the 6–31+G(d) basis set.