Synthesis of dimethoxytetraarylbenziporphyrins

ORGN 147

Joseph T. Szymanski, Department of Chemistry, Illinois State University, Campus Box 4160, Normal, IL 61760 and Timothy D. Lash, Department of Chemistry, Illinois State Universtiy, Normal, IL 61790-4160.
A series of dimethoxybenziporphyrins have been prepared in three steps from 1,3-dimethoxybenzene or 2-methyl-1,3-dimethoxybenzene. Although the free bases are not aromatic, upon protonation there is evidence of a macrocyclic ring current and an increase in aromatic character. Reaction with nickel(II) acetate in CHCl3/CH3OH affords the corresponding organometallic derivatives. Further studies are in progress to exploit this direct route to these carbaporphyrinoids