Electrocatalytic oxidative cleavage of electron-deficient substituted stilbenes in acetonitrile-water employing a new high oxidation potential electrocatalyst. An electrochemical equivalent of ozonolysis.

A series of symmetrical and unsymmetrical stilbenes bearing two or more strong electron-withdrawing groups were oxidatively cleaved to the corresponding aldehydes in high yield by electrocatalytic anodic oxidation in aqueous acetonitrile employing a new high oxidation potential triphenylamine electrocatalyst. The oxidations apparently involve the corresponding 1,2-diols, which are also converted to aldehydes in high yield under the same conditions.