The Chemistry of Pyrrolic Compounds. LX. Reaction of Photoprotoporphyrin-IX Dimethyl Ester With Cyanide Ion

Abstract

Reaction of the a,β-unsaturated aldehyde system of photoprotoporphyrin IX dimethyl ester with cyanide ion yields a porphyrin with an acetamide side chain. Mechanistically, the reaction can be viewed as an intramolecular hydrolysis of the cyanide adduct driven by a return to a macrocycle with the porphyrin conjugation pathway.