Meso-Substituted Corroles from Nitrosoalkenes and Dipyrromethanes

Abstract

The synthesis of bilanes and hexapyrroles containing an oxime functionality, prepared by two and three consecutive hetero-Diels-Alder reactions (or conjugated additions) between nitrosoalkenes and dipyrromethanes, is described. Bilanes underwent oxidative macrocyclization to afford a new class of trans-A2B-corroles. Porphyrins could also be obtained by reacting bilanes with aldehydes in the presence of trifluoroacetic acid, followed by an oxidative step.