Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 1, Pages 251-260Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo048359j
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In the competitive peroxidation of mixtures of two alkenes with Co(II)/O-2/Et3SiH, it was found that the relative reactivities of the alkene substrates are influenced by three major factors:. (1) relative stability of the intermediate carbon-centered radical formed by the reaction of the alkene with HCo(III) complex, (2) steric effects around the C=C double bond, and (3) electronic factors associated with the C=C double bond. Consistent with results from simple alkenes, the chemo-and regioselective peroxidation of dienes was also realized. Depending on the diene structure, the product included not only the expected acyclic unsaturated triethylsilyl peroxides but also 1,2-dioxolane and 1,2-dioxane derivatives via intramolecular cyclization of the unsaturated peroxy radical intermediates.
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