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 w ere synthesized and evaluated as catalysts for hydrocarbon oxidation with H 2O2; iron porphyrins bearing five or six beta -nitro groups were the best c atalysts for cyclooctene epoxidation and adamantane or anisole hydroxylatio n without need of a cocatalyst, and led to very different regioselectivitie s with either H2O2 or PhIO as oxidants, as shown by an unusual ortho-hydrox ylation of alkoxybenzenes highly favored in the H2O2-dependent oxidations.