Metal-free reductive cleavage of benzylic esters and ethers, fragmentations result from single and double electron transfers

Doni, Eswararao and O'Sullivan, Steven and Murphy, John A (2013) Metal-free reductive cleavage of benzylic esters and ethers, fragmentations result from single and double electron transfers. Angewandte Chemie International Edition, 52 (8). pp. 2239-2242. ISSN 1433-7851

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Abstract

The mechanisms for the reductive cleavage of benzylic esters and ethers by neutral organic electron donor 1 are different (see scheme). Products isolated from the cleavage of benzylic ethers result from the transfer of two electrons, without the intermediacy of benzyl radicals, which are believed to be intermediates in the reductive cleavage of benzylic esters.