Rothemund and Adler-Longo reactions revisited: synthesis of tetraphenylporphyrins under equilibrium conditions

…, HC Hsu, PC Kearney, AM Marguerettaz

Index: Lindsey, Jonathan S.; Schreiman, Irwin C.; Hsu, Henry C.; Kearney, Patrick C.; Marguerettaz, Anne M. Journal of Organic Chemistry, 1987 , vol. 52, # 5 p. 827 - 836

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Citation Number: 1337

Abstract

We present a new synthetic strategy for preparing tetraphenylporphyrins that should greatly expand synthetic entries into porphyrin containing model systems. Pyrrole and the desired benzaldehyde react reversibly at room temperature with trace acid catalysis to form the cyclic tetraphenylporphyrinogen at thermodynamic equilibrium. An oxidant is then added to irreversibly convert the porphyrinogen to the porphyrin. The greater stability of the cyclic ...