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Metal-Free Reductive Cleavage of Benzylic Esters and Ethers: Fragmentations Result from Single and Double Electron Transfers

Authors

  • Eswararao Doni,

    1. WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL (UK)
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  • Steven O'Sullivan,

    1. WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL (UK)
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  • Prof. Dr. John A. Murphy

    Corresponding author
    1. WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL (UK)
    • WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL (UK)===

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  • We thank ORSAS and the University of Strathclyde for funding and the EPSRC National MS Service Centre for mass spectra.

Abstract

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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.

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