Epoxidation of simple allenes. Role of cyclopropanones as reactive intermediates

JK Crandall, WH Machleder…

Index: Crandall,J.K. et al. Journal of Organic Chemistry, 1973 , vol. 38, p. 1149 - 1154

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Citation Number: 25

Abstract

The peracid oxidation of tetramethylallene, 1, l-dimethylallene, and 1, 2-cyclononadiene has been studied. The products of these reactions are rationalized in terms of initial formation of an allene oxide followed by competitive partitioning of this reactive species between valence isomerism to the related cyclopropanone and further oxidation to a dioxaspiropentane derivative. In addition to combining with the carboxylic acid generated during the oxidation ...