Indirect electrochemical oxidation of cyclic ketones: Strong influence of ring size on the result of the reaction

F Barba, MN Elinson, J Escudero, SK Feducovich

Index: Barba, Fructuoso; Elinson, Michail N.; Escudero, Jose; Feducovich, Sergey K. Tetrahedron Letters, 1996 , vol. 37, # 32 p. 5759 - 5762

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Citation Number: 12

Abstract

The result of the indirect electrochemical oxidation of cyclic ketones in methanol in the undivided cell in the presence of sodium iodide depends on the ring size. Cyclopentanone affords 2, 2-dimethoxycyclopentanone. While cyclohexanone gives rise 2, 2-dimethoxycyclo- hexanol, and cyclic ketones with higher ring size undergo new type of the electrochemically induced Favorskii rearrangement with the formation of methyl cycloalkencarboxylates ...