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Paper | Special issue | Vol 54, No. 2, 2001, pp.705-720
Published online, 1st January, 1970
DOI: 10.3987/COM-00-S(I)48
Preparation of Meso-unsubstituted Porphyrins Substituted with Mono- and Tetraformyl and Other Electron- withdrawing Groups

Yumiko Fumoto, Hidemitsu Uno, Takashi Murashima, and Noboru Ono*

*Department of Chemistry, Faculty of Science, Ehime University, Matsuyama 790-8577, Japan


A meso-unsubstituted porphyrin having a formyl group was synthesized both from a mono(ethoxycarbonyl)porphyrin by reduction with LiAlH4 followed by oxidation with MnO2 and from a monocyanoporphyrin by reduction with DIBALH. The monoethoxycarbonyl and monocyanoporphyrins were prepared by the acid catalyzed mixed condensation of the corresponding 4-ethoxycarbonyl- and 4-cyano-2-(hydroxymethyl)pyrroles with 3-mesityl-4-methyl-2-(hydroxymethyl)pyrrole. A porphyrin with four formyl groups at the β-positions was prepared from ethyl 4-(dithiolan-2-yl)-3-methylpyrrole-2-carboxylate by the sequential treatment of LiAlH4, p-TsOH, and NBS. Cyclic voltammetry and UV-VIS spectroscopic analyses of these porphyrins revealed the highly electron-deficient property of the porphyrin chromophore.