✦ LIBER ✦

Reactivity of a trivalent phosphorus radical cation as an electrophile toward pyridine derivatives

✍ Scribed by Shinro Yasui; Kosei Shioji; Munekazu Tsujimoto; Atsuyoshi Ohno

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 185 KB
Volume: 11
Category: Article
ISSN: 1042-7163
DOI: 10.1002/(sici)1098-1071(2000)11:2<152::aid-hc11>3.0.co;2-0

No coin nor oath required. For personal study only.

✦ Synopsis

The reaction of methylviologen (MV ‫ם2‬ ) with tributylphosphine (1p) and diethylphenylphosphine (1q) in the presence of an alkyl-substituted pyridine (2) was found to take place through a singleelectron transfer (SET) from 1 to MV ‫ם2‬ followed by nucleophilic attack by 2 on the resulting phosphine radical cation 1 ‫ם⅐‬ . Kinetic examination showed that, in the transition state for the reaction of 1 ‫ם⅐‬ with 2, an unpaired electron is largely delocalized to the pyridine moiety.