Dechlorination of substituted trichloromethanes by an iron(II) porphyrin

Iron(II) porphyrins complex with many organochlorine compounds and oxidize by dechlorinating them. For a series of trichloromethyl derivatives, CCl3R (R = NO2, CHCl2, CN, Cl, COO-, CH3, H, C(O)NH2, and CH2OH), heme oxidation occurred in two consecutive steps: heme-CCl3R complexation, and (usually slower) inner-sphere electron transfer. Stability of the intermediate . CCl2R radical, which is strongly correlated with the ability of the R group to delocalize electron density, governed the overall electron transfer rate.