Colorful Friedel-Crafts chemistry of meso-tetraarylporphyrins. An unexpected route to porphyrinic spiro dimers |
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Authors: | Jeandon Christophe Ruppert Romain Richeter Sébastien Callot Henry J |
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Institution: | Faculté de Chimie, UMR 7123 CNRS, Université Louis Pasteur, 1 rue Blaise Pascal, 67000 Strasbourg, France. |
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Abstract: | 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. reaction: see text] |
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