Iron polynitroporphyrins bearing up to eight beta-nitro groups as interesting new catalysts for H2O2-dependent hydrocarbon oxidation: unusual regioselectivity in hydroxylation of alkoxybenzenes.

A series of iron porphyrins bearing one to eight beta-nitro substituents were synthesized and evalauted as catalysts for hydrocarbon oxidation with H2O2; iron porphyrins bearing five or six beta-nitro groups were the best catalysts for cyclooctene epoxidation and adamantane or anisole hydroxylation without need of a cocatalyst, and led to very different regioselectivities with either H2O2 or PhIO as oxidants, as shown by an unusual ortho-hydroxylation of alkoxybenzenes highly favored in the H2O2-dependent oxidations.