Abstract
Abstract : Several aspects of chemistry related to autoxidation, peroxy free radicals, and peroxides have been explored. Methods for preparation of complex unsaturated hydroperoxides have been developed and peroxy radicals derived from these hydroperoxides were studied as models for polyunsaturated fatty acid and polyolefin (i.e., polybutadiene and polyisoprene) autoxidation. We have established that peroxy radical cyclization and bicyclization occurs in models of polyunsaturated fatty acid oxidation and a new type of cyclization, serial cyclization, has been observed in polybutadiene oxidation models. Kinetic and stereochemical aspects of these cyclization reactions have been explored. The free radical oxidation of polyunsaturated fatty acids has been studied mechanistically. In particular, we believe that the H atom donating ability of the medium in which oxidation occurs is an important factor in determining the partitioning of peroxy free radicals between competitive pathways (i.e., beta scission and cyclization). The results of these studies provide a firm basis for understanding the degradation of materials, foodstuffs, etc. (Author)
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