Oxidation of. alpha.-ketoacyl derivatives. Rearrangement of pyruvates to malonates

ML Rueppel, H Rapoport

Index: Rueppel,M.L.; Rapoport,H. Journal of the American Chemical Society, 1972 , vol. 94, p. 3877 - 3883

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Citation Number: 31

Abstract

Abstract: a-Keto esters and amides undergo oxidative rearrangement when treated with periodate at pH 7-9 to give malonic acid derivatives. When the amide is cyclic (a- ketolactams), ring contraction occurs. The major pathway of this oxidative rearrangement of cy-ketoacyl derivatives probably involves the cleavage of an intermediate a- hydroxycyclopropanone to give the observed product. In addition, a minor path through a ...