corrole and chlorin

The insertion of a -NO2 group onto the corrole framework represents a key step for subsequent synthetic manipulation of the macrocycle based on the chemical versatility of such a functionality. Here we report results of the investigation of a copper 3-NO2-triarylcorrolate in nucleophilic aromatic substitution reactions with "active" methylene carbanions, namely diethyl malonate and diethyl 2-chloromalonate. Although similar reactions on nitroporphyrins afford chlorin derivatives, nucleophilic attack on carbon-2 of corrole produces 2,3-difunctionalized Cu corrolates in acceptable yields (ca. 30%), evidencing once again the erratic chemistry of this contracted porphyrinoid.

Topics: Chemistry Techniques, Synthetic; Copper; Crystallography, X-Ray; Magnetic Resonance Spectroscopy; Malonates; Molecular Structure; Organometallic Compounds; Porphyrins; Pyrroles; Spectrophotometry, Ultraviolet