In situ EPR studies of reaction pathways in Titania photocatalyst-promoted alkylation of alkenes

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Shona Rhydderch, Russell F Howe

Abstract

In situ EPR spectroscopy at cryogenic temperatures has been used to observe and identify paramagnetic species produced when titania is irradiated in the presence of reactants used in the photocatalytic alkylation of maleimide with t-butyl carboxylic acid or phenoxyacetic acid. It is shown that maleimide acts as an acceptor of conduction band electrons. Valence band holes oxidise t-butyl carboxylic acid to the t-butyl radical and phenoxyacetic acid to the phenoxyacetic acid radical cation. In the presence of maleimide, the phenoxymethyl radical is formed from phenoxyacetic acid. The relevance of these observations to the mechanisms of titania photocatalyst-promoted alkylation of alkenes is discussed.

References

Jan 26, 2005·Journal of Chemical Information and Modeling·Tomasz SpałekZbigniew Sojka
Jul 21, 2006·The Journal of Physical Chemistry. B·T BergerJ T Yates
Jul 27, 2006·The Journal of Physical Chemistry. B·Deanna C HurumMarion C Thurnauer
Aug 8, 2012·Journal of the American Chemical Society·David W ManleyJohn C Walton
May 23, 2013·Physical Chemistry Chemical Physics : PCCP·Mario ChiesaElio Giamello
Jan 21, 2014·The Journal of Organic Chemistry·David W ManleyChristopher O'Rourke

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Citations

Dec 15, 2015·Beilstein Journal of Organic Chemistry·David W Manley, John C Walton

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Methods Mentioned

BETA
NMR

Software Mentioned

SIM32

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