Tetrahedron p. 2021 - 2030 (1998)
Update date:2022-08-05
Topics:
Brueckner, Christian
Xie, Lily Y.
Dolphin, David
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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