Abstract
Iron(III) porphyrins efficiently catalyze the epoxidation of alkenes and the hydroxylation of alkanes by iodosylbenzenes and peracids, most likely by the same mechanisms utilized by cytochrome P-450 enzymes. The synthetic catalysts mimic the enzymes in product stereospecificity, 1 the accompanying rearrangements, 2 and the suicide labelling which results in N-alkylhemin formation.3
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References
J. P. Collman, T. Kodadek, and J. I. Brauman, Oxygenation of styrene by cytochrome P-450 model systems: a mechanistic study, J. Am. Chem. Soc. 108:2588 (1986).
J. T. Groves and R. S. Myers, Catalytic asymmetric epoxidations with chiral iron porphyrins, J. Am. Chem. Soc. 105:5791 (1983).
T. Mashiko, D. Dolphin, T. Nakano, and T. G. Traylor, N-alkylporphyrin formation during the reactions of cytochrome P-450 model systems, J. Am. Chem. Soc. 107:3735 (1985).
T. G. Traylor, T. Nakano, B. E. Dunlap, P. S. Traylor, and D. Dolphin, Mechanisms of hemin-catalyzed alkene epoxidation. The effect of catalyst on the regiochemistry of epoxidation, J. Am. Chem. Soc. 108:2782 (1986).
T. G. Traylor and A. R. Miksztal, Mechanisms of hemin-catalyzed epoxidations: electron transfer from alkenes, J. Am. Chem. Soc. 109:2770 (1987).
J. P. Collman, T. Kodadek, S. A. Raybuck, J. I. Brauman, and L. M. Papazian, Mechanism of oxygen atom transfer from high valent iron to olefins: implications to the biological epoxidation of olefins by cytochrome P-450, J. Am. Chem. Soc. 107:4343 (1985).
T. G. Traylor, T. Nakano, A. R. Miksztal, and B. E. Dunlap, Transient formation of N-alkylhemins during hemin-catalyzed epoxidation of norbornene. Evidence concerning the mechanism of epoxidation, J. Am. Chem. Soc. 109:3625 (1987).
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© 1988 Plenum Press, New York
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Traylor, T.G., Dunlap, B.E., Miksztal, A.R. (1988). Cytochrome P-450 Model Systems: Alkene Oxidation. In: Simic, M.G., Taylor, K.A., Ward, J.F., von Sonntag, C. (eds) Oxygen Radicals in Biology and Medicine. Basic Life Sciences, vol 49. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-5568-7_78
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DOI: https://doi.org/10.1007/978-1-4684-5568-7_78
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