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

Tardieux Catherine | Zendy; Gros Claude P. | Zendy; Guilard Roger | Zendy

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

Author(s) -

Tardieux Catherine,

Gros Claude P.,

Guilard Roger

Publication year - 1998

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570350430

Subject(s) - corrole , chemistry , biliverdin , tetrapyrrole , trifluoroacetic acid , isomerization , oxidative cleavage , photochemistry , acetic acid , yield (engineering) , porphyrin , stereochemistry , organic chemistry , heme , catalysis , materials science , heme oxygenase , metallurgy , enzyme

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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