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 ...
