INDIRECT ELECTROCHEMICAL OXIDATION OF CYCLIC-KETONES - STRONG INFLUENCE OF RING SIZE ON THE RESULT OF THE REACTION

The result of the indirect electrochemical oxidation of cyclic ketones in methanol in the undivided cell in the presence of sodium iodide de pends on the ring size. Cyclopentanone affords 2,2-dimethoxycyclopenta none. While cyclohexanone gives rise 2,2-dimethoxycyclo-hexanol, and c yclic ketones with higher ring size undergo new type of the electroche mically induced Favorskii rearrangement with the formation of methyl c ycloalkencarboxylates containing in the ring on the one carbon atom le ss than starting ketone. So the simple electrocatalytic system can dis tinguish the ring size of cyclic ketones. Copyright (C) 1996 Elsevier Science Ltd.