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Communication | Special issue | Vol 37, No. 1, 1994, pp.213-218
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S30
Some New Porphodimethene Chemistry: Synthesis of meso-Formylporphyrins

José A. S. Cavaleiro, M. Graça, P. M. Neves, Craig J. Medforth, and Kevin M. Smith*

*Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA 95616-5295, U.S.A.

Abstract

Treatment of dipyrromethane-1,9-dicarboxylic acids with triethyl orthoformate and trifluoroacetic acid gives the expected symmetrically substituted porphyrin, along with small amounts of meso-formyl and meso-diformyl-porphyrins. The 5,15 regioselectivity of the formyl groups in the disuhstituted product and NOE experiments suggest that serendipitous formylation takes place at the intermediate porphodimethene stage.