Colorful Friedel-Crafts chemistry of meso-tetraarylporphyrins. An unexpected route to porphyrinic spiro dimers

graphic 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. B...

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Published inOrganic letters Vol. 5; no. 9; pp. 1487 - 1489
Main Authors Jeandon, C, Ruppert, R, Richeter, S, Callot, HJ
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 01.05.2003
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BETA-FORMYLPORPHYRINS
PYRROLIC COMPOUNDS
INTRAMOLECULAR CYCLIZATION
NAPHTHOCHLORINS
PETROPORPHYRINS
RING-SYSTEMS
DERIVATIVES
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Summary:graphic 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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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0342554