N-Alkylporphyrin Formation during the reactions of Cytochrome P-450 Model Systems
Mashiko, T., David Dolphin, Nakano, T., and Traylor, T.G.,
J. Am. Chem Soc.,
5,10,15,20-Tetrakis(2,6-dichlorophenyl)porphinatoiron(III) chloride is an effective catalyst for the hydroxylation of alkanes and the epoxidation of olefins using the oxidant iodosopentafluorobenzene. When 4,4-dimethyl-1-pentene is the substrate, the principal product is the corresponding epoxide. However, suicide inhibition paralleling the in vivo destruction of cytochrome P 450 enzymes occurs to give, after workup, the N-alkylporphyrin, 21-(4,4-dimethyl-2-hydroxypentyl)-5,10,15,20-tetrakis(2,6-dichlorophenyl)porphine.