Metal Complex-Catalyzed Epoxidation of Olefins by Dioxygen with Co-Oxidation of Aldehydes. A Mechanistic Study

Wonwoo Nam, Hyo Jin Kim, Seong Hoon Kim, Raymond Y.N. Ho, Joan Selverstone Valentine

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199 Scopus citations

Abstract

Mechanistic studies of the oxidation of olefins by dioxygen plus aldehyde in the presence of metal complexes such as metalloporphyrins and metal cyclam complexes have been carried out. Epoxides were the predominant products, with trace amounts of allylic oxidation products. cis-Stilbene was oxidized to a mixture of cis- and trans-stilbene oxides. It is concluded from this study that the principal role of the metal complexes is to aid in the initiation step for the free radical autoxidation of the aldehyde and that acylperoxy radicals generated in the autoxidation reaction (or metal complexes formed by complexation of the acylperoxy radicals) are the active epoxidizing agents.

Original languageEnglish
Pages (from-to)1045-1049
Number of pages5
JournalInorganic Chemistry
Volume35
Issue number4
DOIs
StatePublished - 1996

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