Intramolecular Reactions of Unsaturated Peroxides and Peroxy Radicals.

Abstract

Abstract : The mechanisms of free radical oxidation of organic compounds have been studied. It has been determined that unsaturated peroxy radicals will undergo cyclization reactions leading to a variety of cyclic peroxide compounds. It appears that peroxy radicals derived from naturally occurring organic compounds such as rubbers, fats, and oils, are converted into a variety of compounds that contain the cyclic peroxide nucleus. Simple model compounds that permit the study of the peroxy radical cyclization have been examined. These model studies show that, in addition to cyclic peroxides, a variety of compounds that include epoxides and alcohols are formed by free radical mechanisms. Thus, primary products to be expected from autoxidation of natural materials such as fats and rubbers and mono and bicyclic peroxides and epoxy alcohols. (Author)