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On corrole chemistry. An isomerization study and oxidative cleavage of the corrole macroring to a biliverdin structure

✍ Scribed by Catherine Tardieux; Claude P. Gros; Roger Guilard

Publisher: Journal of Heterocyclic Chemistry
Year: 1998
Tongue: English
Weight: 400 KB
Volume: 35
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570350430

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✦ Synopsis

Abstract

In the present paper, we report the synthesis of free 5‐ and 10‐monophenylcorroles, 4 and 3 respectively as well as the first example of molecular oxygen oxidation of the corrole macrocycle identified as an open chain tetrapyrrole (biliverdin) structure 7. Reaction of 1 and 2 in acetic acid leads to a mixture of two a,c‐biladienes 3b and 4b and therefore to a mixture of two corrole isomers 3 and 4. Reaction of 1 and 2 in trifluoroacetic acid leads only to the symmetrical corrole isomer 3 in 41% yield.

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On Corrole Chemistry. An Isomerization Study and Oxidative Cleavage of the Corrole Macroring to a Biliverdin Structure. -Free monophenyl-substituted corroles are obtained by an isomerization reaction. Reaction of (I) with (II) in acetic acid leads to a mixture of two a,c-biladienes forming the cor