An experimental and theoretical investigation of the regioselective cleavage of aromatic sulfones

Abstract

Aromatic sulfones activated by strongly electron-withdrawing groups were reduced electrochemically. The radical anions produced were shown to be fairly stable. Cleavage reactions are so slow that other chemical reactions (protonation, dimerization, etc.) may take place. A theoretical study at the B3LYP level underlines that bond cleavage does not depend on the presence or not of electron-withdrawing groups substituted on the phenyl ring in the para position.