✦ LIBER ✦

A convenient procedure for moderate-scale Rothemund synthesis of lipophilic porphyrins: an alternative to the Adler–Longo and Lindsey methodologies

✍ Scribed by Maxwell J. Crossley; Pall Thordarson; (the late) J. Patrick Bannerman; Philip J. Maynard

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 91 KB
Volume: 02
Category: Article
ISSN: 1088-4246
DOI: 10.1002/(sici)1099-1409(199811/12)2:6<511::aid-jpp102>3.0.co;2-e

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✦ Synopsis

Rothemund synthesis of porphyrins is conveniently achieved using p-toluenesulfonic acid-catalysed reaction between pyrrole and aldehyde with azeotropic removal of the water formed in the reaction. These conditions are suitable for moderate-scale reactions and involve an easy work-up. In this way, 5,10,15,20-tetraheptylporphyrin (2), 5,10,15,20-tetrakis(3,5-di-tert-butylphenyl)porphyrin (3), 5,10,15,20-tetra-tert-butylporphyrin (4) and 5,10,15,20-[pyromellitoyl(tetrakis-o-oxyethoxyphenyl)]por-phyrin (5) were prepared in moderate to good yields.