meso(Methine) functionalization of octa-alkylporphyrins

Abstract

meso-Acetoxymethylocta-alkylporphyrins [e.g.(1), (7), and (8)] react with a variety of nucleophiles such as alcohols (to give the corresponding alkoxymethylporphyrins), amines (yielding aminomethylporphyrins), and Grignard reagents (to give meso-alkylporphyrins). Treatment of the meso-acetoxymethylporphyrins with thiol reagents accomplishes reduction to give the meso-methylporphyrin rather than the sulphide. Making use of these meso-functionalization reactions, potential cytochrome P450 models and a model for the tense form of hemoglobin are synthesized.