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Colorful Friedel−Crafts Chemistry of meso-Tetraarylporphyrins. An Unexpected Route to Porphyrinic Spiro Dimers

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journal contribution
posted on 02.04.2003, 00:00 by Christophe Jeandon, Romain Ruppert, Sébastien Richeter, Henry J. Callot
Under Friedel−Crafts conditions, meso-tetraarylporphyrins give porphyrin spiro dimers in good yield. This reaction involves acylation, acid-catalyzed cyclization, and dimerization. A stable dimer possessing three additional six-membered rings could be isolated and its structure determined. By modifying the substrate and reagents, intermediates could be isolated and characterized. The reactivity of the substrates, the side-reactions, and the concentration requirements to form the dimers, all explain why this reaction remained apparently unexplored in the widely used meso-tetraarylporphyrin series.

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