Journal of the American Chemical Society

New synthetic reactions. Oxidative decarboxylation of. alpha.-methylthiocarboxylic acids, new approach to acyl anion and ketene synthons

BM Trost, Y Tamaru

Index: Trost,B.M.; Tamaru,Y. Journal of the American Chemical Society, 1977 , vol. 99, # 9 p. 3101 - 3113

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Citation Number: 74

Abstract

Abstract: a-Methylthiocarboxylic acids, available by the direct sulfenylation of the dianions of carboxylic acids or hydrolysis of sulfenylated esters, are rapidly transformed to the acetal or ketal of the noraldehyde or ketone. The effect of solvent on this reaction is substantial with methanol or ethanol preferred. The application to a fatty acid and 3-oxobisnorcholen-22-al illus-trates some of the potential of the method in natural products. This approach allows ...

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