Pub No:
339
Title:
The Reductive Coupling of 2-Cyanopyrroles: A Study Pertaining to the Mechanism of Formation of Porphocyanines
Authors:
Bruckner, C., Xie, L.Y., and David Dolphin
Journal:
Tetrahedron
Year:
1998
Pages:
54, 2021-2030
Abstract:
2-Cyanopyrrole was found to form (2-pyrrolylmethene)-(2-pyrrolylmethyl)imine 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 27Al-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

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