Homolytic cleavage of peroxide bonds via a single electron transfer of a frustrated Lewis pair.

Chem Commun (Camb)

Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario M5S 3H6, Canada.

Published: July 2018

Single electron transfer (SET) reactions are effected by the combination of a MesP/B(CF) frustrated Lewis pair with benzoyl peroxide derivatives. The resulting homolytic cleavage of the peroxide bonds affords the radical salts [MesP˙][RCOOB(CF)] (R = Ph 1, p-BrCH2, p-MeCH3). These species react with PhSnH to give [MesPH][RCOOB(CF)] (R = Ph 10, p-BrCH11, p-MeCH12) and (PhSn). The mechanism of these SET reactions is discussed in light of control experiments and DFT calculations.

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Source
http://dx.doi.org/10.1039/c8cc03522aDOI Listing

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