Examination of reaction conditions for two-step, one-flask syntheses of meso-substituted corroles via dipyrromethane-dicarbinol and pyrrole

ORGN 144

G. Richard Geier III, Jeffery Forris Beecham Chick, Jennifer B. Callinan, Christopher G. Reid, and Waldemar Auguscinski. Department of Chemistry, Colgate University, 13 Oak Drive, Hamilton, NY 13346

The acid catalyzed condensation of dipyrromethane-dicarbinol + pyrrole leading to meso-substituted corrole was investigated. A systematic examination of acid catalysts, acid concentration, equivalents of pyrrole, condensation time, and oxidation conditions was performed via analytical scale reactions monitored for yield of corrole by UV-vis spectroscopy. The results of the optimal analytical scale experiments were confirmed by preparative scale reactions. A variety of corroles bearing meso-substituents in defined locations were prepared. The crude reaction mixtures were devoid of porphyrin byproduct or other evidence of undesired substituent scrambling. Isolated yields of corrole ranged from 18-80% depending on the substituents. These results complement and extend previously reported reaction conditions for the synthesis of meso-substituted corroles via dipyrromethane-dicarbinol + pyrrole.

New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics 8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster Division of Organic Chemistry The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004