Unexpected Hofmann elimination in the benzophenone-(phenylthio)acetic tetrabutylammonium salt photoredox system |
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| Authors: | Wrzyszczyński Andrzej Pietrzak Marek Bartoszewicz Jarogniew Kozubek Halina Hug Gordon L Marciniak Bronislaw Paczkowski Jerzy |
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| Affiliation: | Faculty of Chemical Technology and Engineering, University of Technology and Agriculture, Bydgoszcz, Poland. |
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| Abstract: | 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. |
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