beta-Hydroxyalkyl sigma-Metalloporphyrins: Models for Epoxide and Alkene Generation from Cytochrome P-450
David Dolphin, Matsumoto, A., and Shortman, C.
J. Am. Chem. Soc.
Β-Hydroxyalkyl σ-metalloporphyrins (Fe and Co) may be prepared by alkyl group migration following reduction of the corresponding N-alkylporphyrins or by direct oxidative addition to a bromohydrin. The formation of an alkoxide from the ?-alkyl complex generates epoxide and small amounts of alkene. It is suggested that this chemistry mimics that of small alkenes which show stereospecific H exchange at the terminal methylene of both epoxide and recovered alkene when being metabolized by cytochrome P 450 (LM2).