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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
. 1988 Feb;85(3):641–644. doi: 10.1073/pnas.85.3.641

Observations and comments on the mechanism of epoxidation of alkenes by manganese(III) porphyrins with hypochlorite.

R W Lee 1, P C Nakagaki 1, P N Balasubramanian 1, T C Bruice 1
PMCID: PMC279610  PMID: 2829197

Abstract

The kinetics of olefin epoxidation in a methylene chloride/water biphase containing a phase-transfer agent with hypochlorite as oxygen transfer reagent and manganese(III) tetraphenylporphyrin catalysts has been reinvestigated. The results do not support the accumulation of an intermediate composed of an alkene and a hypervalent metaloxo porphyrin. Second-order rate constants for oxygen transfer from hypochlorite to the manganese porphyrin, comproprotionation of the hypervalent manganese-oxo porphyrin with manganese(III) porphyrin, and olefin epoxidation by the hypervalent manganese-oxo porphyrin were obtained from experiments in a wet organic monophase.

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Selected References

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

  1. Collman J. P., Brauman J. I., Meunier B., Raybuck S. A., Kodadek T. Epoxidation of olefins by cytochrome P-450 model compounds: mechanism of oxygen atom transfer. Proc Natl Acad Sci U S A. 1984 May;81(10):3245–3248. doi: 10.1073/pnas.81.10.3245. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Collman J. P., Kodadek T., Raybuck S. A., Meunier B. Oxygenation of hydrocarbons by cytochrome P-450 model compounds: modification of reactivity by axial ligands. Proc Natl Acad Sci U S A. 1983 Nov;80(22):7039–7041. doi: 10.1073/pnas.80.22.7039. [DOI] [PMC free article] [PubMed] [Google Scholar]

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