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Further studies on the reduction of benzylic alcohols by hypophosphorous acid/iodine

Further studies on the reduction of benzylic alcohols by hypophosphorous acid/iodine

  1. Quantum Dude
    Hydrogen iodide, generated (and regenerated) in situ by the action of iodine upon
    hypophosphorous acid, was found to reduce a variety of aryl carbinols to the corresponding
    diphenylmethanes under mild conditions. The generality of the reaction was explored by
    extension to several diols, heterocyclic alcohols, and allylic alcohols. Several lines of evidence,
    including occasional isolation of alkyl iodides, dependence of the rate of reduction upon
    substituent effects, and isolation of ethers and esters in the early stages of reduction, reveal that
    the first step in the reduction process is conversion of the alcohol to a carbocation. Isolation of
    dimers from cinnamyl alcohol and 1-phenyl-2-propen-1-ol demonstrates the intermediacy of
    radical intermediates in at least some reductions.