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Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1984 May;81(10):3245–3248. doi: 10.1073/pnas.81.10.3245

Epoxidation of olefins by cytochrome P-450 model compounds: mechanism of oxygen atom transfer.

J P Collman, J I Brauman, B Meunier, S A Raybuck, T Kodadek
PMCID: PMC345259  PMID: 6587349

Abstract

The mechanism of the Mn(III) porphyrin-catalyzed epoxidation of olefins by lithium hypochlorite is examined. The active oxidant is thought to be a high-valent manganese-oxo complex. It is shown that a relatively stable intermediate is reversibly formed upon interaction of the olefin and the oxo complex. The decomposition of this intermediate to Mn(III) porphyrin and epoxide is the rate-determining step of the catalytic cycle. Some analogies to the biochemical epoxidation of olefins catalyzed by cytochrome P-450 are discussed.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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