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The reductive coupling of 2-cyanopyrroles: A study pertaining to the mechanism of formation of porphocyanines

TitleThe reductive coupling of 2-cyanopyrroles: A study pertaining to the mechanism of formation of porphocyanines
Publication TypeJournal Article
Year of Publication1998
AuthorsBruckner, C, Xie, LY, Dolphin, D
JournalTetrahedron
Volume54
Pagination2021-2030
Date PublishedMar
Type of ArticleArticle
ISBN Number0040-4020
KeywordsCENTERED TEMPLATE REACTIONS, COMPLEX, CONVENIENT, EXPANDED TETRAPYRROLIC MACROCYCLE
Abstract

2-Cyanopyrrole was found to form (2-pyrrolylmethene)-(2-pyrrolylmethyl)im when treated with lithium aluminum hydride (LAH), followed by a mild work-up. A plausible mechanism of this reductive coupling was inferred from a series of experiments, including Al-27-NMR deuteration experiments, and the reduction of variously substituted cyanopyrroles. The mechanism, a metal chelate mediated dimerization, may be the key to understanding porphocyanine synthesis via the LAH reduction of 1,9-dicyanodipyrromethanes. (C) 1998 Elsevier Science Ltd. All rights reserved.

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