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✦   LIBER   ✦

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

✍ Scribed by Christian Brückner; Lily Y. Xie; David Dolphin

Book ID
104208322
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
776 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

2-Cyanopyrrole was found to form (2-pyrrolyhnetheoe)-(2-pyxmlyhnethyl)imine when treated witi lithium ahuninum hydride (LAH). followed by a mild work-up. A plausible mechanism of this reductive coupling was inferred from a series of experiments, including ~~AI-NMR, deuteration experiments, and the reduction of variously substituted cyawpynn les. The mechanism, a metal chelate mediateddimekation, may be the key to understanding porphocyanine synthesis via the LAH reduction of 1.9dicyanodipyrmmeUmnes.

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In a recent paper' Mustafa et al. reported the reaction of triphenylwsphine (I) with pbenzoquinonedibenzesulf~~de (a) in a dry benzene solution to yield a violet colored precipitate. Upon expo sure to the atmosphere, the color of the precipitate faded and triphenylphosphine oxide (2) was isolated fr