Stereochemistry of olefin and fatty acid oxidation. Part 1. Autoxidation of hexene and hepta-2,5-diene isomers

Abstract

The stereochemistry of the autoxidation of hex-1-ene, cis- and trans-hex-2-ene, cis- and trans-hex-3-ene, and of the three geometrical isomers of hepta-2,5-diene, has been determined by the reduction of the hydroperoxides produced and analysis of the resulting allylic alcohols. The relative proportions of the isomeric hydroperoxides are explicable in terms of the conformations of the parent olefins which are capable of giving delocalised radicals on hydrogen abstraction.