Perchlorinated and Other Highly Chlorinated meso-Tetraphenylporphyrins
Wijesekera, T., Matsumoto, A., Lexa, D., and David Dolphin
Angewandte Chemie I.E.
FeLCl (H2L = meso-tetra(2,6-dichlorophenyl)porphyrin, tetra(perchlorophenyl)-porphyrin chlorinated by Cl2 gas in the presence of FeCl3 in o-C6H4Cl2 to give FeL1Cl (H2L1 = meso-tetra(2,6-dichlorophenyl)octachloroporphyrin, tetra(perchlorophenyl)-octachloroporphyrin). Chlorination of Fe(TPP)Cl (H2TPP = tetraphenylporphyrin) by Cl2/FeCl3 led to decomposition of the macrocycle. Fe(TPP)Cl and H2TPP were only partially chlorinated by N-chlorosuccinimide (I). Ni(TPP) reacted with I in o-C6H4Cl2 to give NiL2 (H2L2 = octachloroporphyrin). Attempted chlorination of M(TPP) (M = Cu, Zn) led to ring opening. The effect of chlorination of the porphyrin coordinated to Fe was studied on the oxidation and reduction potentials in the presence of Cl- and Ag+.