Anomalous ozone degradations of 1-chloro substituted conjugated dienes in methanol

Abstract

Diozonolyses in methanol of (E)-4-chloro-2,3-dimethyl-1,3-hexadiene (4a) and of (4E)-5-chloro-3,4-dimethyl-2,4-heptadiene (4b) resulted in complete cleavage of the double bonds and of the single bonds of the respective diene systems. The course of these anomalous cleavage reactions has been established by step-wise ozonolyses of these dienes, and by the identification of labile methoxy hydroperoxides as intermediates.