THE REDUCTIVE COUPLING OF 2-CYANOPYRROLES - A STUDY PERTAINING TO THEMECHANISM OF FORMATION OF PORPHOCYANINES

Authors
BRUCKNER C XIE LY DOLPHIN D
Citation
C. Bruckner et al., THE REDUCTIVE COUPLING OF 2-CYANOPYRROLES - A STUDY PERTAINING TO THEMECHANISM OF FORMATION OF PORPHOCYANINES, Tetrahedron, 54(10), 1998, pp. 2021-2030
Citations number
45
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
10
Year of publication
1998
Pages
2021 - 2030
Database
ISI
SICI code
0040-4020(1998)54:10<2021:TRCO2->2.0.ZU;2-D
Abstract
2-Cyanopyrrole was found to form (2-pyrrolylmethene)-(2-pyrrolylmethyl )im when treated with lithium aluminum hydride (LAH), followed by a mi ld work-up. A plausible mechanism of this reductive coupling was infer red from a series of experiments, including Al-27-NMR deuteration expe riments, and the reduction of variously substituted cyanopyrroles. The mechanism, a metal chelate mediated dimerization, may be the key to u nderstanding porphocyanine synthesis via the LAH reduction of 1,9-dicy anodipyrromethanes. (C) 1998 Elsevier Science Ltd. All rights reserved .