Journal of the American Chemical Society

Kinetics of the base-catalyzed decomposition of. alpha.-hydroperoxy ketones

Y Sawaki, Y Ogata

Index: Sawaki,Y.; Ogata,Y. Journal of the American Chemical Society, 1975 , vol. 97, # 24 p. 6983 - 6989

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Citation Number: 37

Abstract

Abstract: The alkoxide-catalyzed decomposition of 15 a-hydroperoxy ketones la-o afforded generally high yields of ketones (80-100%) and esters (70-100%). The high yields of esters show that the a-cleavage reaction proceeds predominantly via an acyclic, carbonyl addition intermediate. The formation of a small amount of carboxylic acid was caused by the reaction of hydroxide ion via the acyclic intermediate rather than via a cyclic 1, 2-dioxetane. The ...