Unexpected Hofmann elimination in the benzophenone-(phenylthio)acetic tetrabutylammonium salt photoredox system.
The triplet state of benzophenone was quenched by the tetrabutylammonium salt of (phenylthio)acetic acid in acetonitrile solutions. The quenching event, following laser flash photolysis, resulted in the formation of a transient ion pair consisting of the benzophenone radical anion and the tetrabutylammonium cation. Subsequently this ion pair decays with the quaternary ammonium cation undergoing a Hofmann elimination to form butane-1 and tributylamine, which were detected in steady-state irradiation. This appears to be the first report of an ion pair consisting of a benzophenone radical anion and an organic cation (nonradical), in addition to the first report of a photoinduced Hofmann elimination in quaternary ammonium ions.
Wrzyszczyński
Andrzej
A
Faculty of Chemical Technology and Engineering, University of Technology and Agriculture, Bydgoszcz, Poland.
Pietrzak
Marek
M
Bartoszewicz
Jarogniew
J
Kozubek
Halina
H
Hug
Gordon L
GL
Marciniak
Bronislaw
B
Paczkowski
Jerzy
J