A Facile and Reliable Method for the Synthesis of Tetrabenzoporphyrin from 4,7-Dihydroisoindole

A Facile and Reliable Method for the Synthesis of Tetrabenzoporphyrin from 4,7-Dihydroisoindole

A new route to tetrabenzoporphyrins from the closest possible precursor of the unstable isoindole was developed. A key feature of this route is a dramatic facilitation of thearomatization of annelated rings, which is the most serious bottleneck in previous syntheses of tetrabenzoporphyrins. The capa...

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Bibliographic Details
Published in:European Journal of Organic Chemistry Vol. 2007; no. 21; pp. 3468 - 3475
Main Authors: Filatov, Mikhail A., Cheprakov, Andrei V., Beletskaya, Irina P.
Format: Book Review Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 01-07-2007
WILEY‐VCH Verlag
Subjects:
Dipyrromethanes
Nitrogen heterocycles
Porphyrinoids
Tetrabenzoporphyrins
π-Extended porphyrins
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Summary:A new route to tetrabenzoporphyrins from the closest possible precursor of the unstable isoindole was developed. A key feature of this route is a dramatic facilitation of thearomatization of annelated rings, which is the most serious bottleneck in previous syntheses of tetrabenzoporphyrins. The capabilities of the new method are illustrated by the synthesis of meso‐tetraaryltetrabenzoporphyrins, as well as the first unambiguous synthesis and characterization of 5,15‐diphenyltetrabenzoporphyrin.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
Bibliography:istex:5BD4CA6B739091C1C62742338DE000CEAED6B8FB
ArticleID:EJOC200700014
Russian Foundation of Basic Research - No. RFBR-04-03-32650-a; No. RFBR-07-03-01121-a
ark:/67375/WNG-MTRGH823-F
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200700014