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Issue 10, 1975
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Electro-organic reactions. Part IV. Preparative aspects of the cathodic hydrogenation of activated carbon–carbon double bonds

Abstract

Compounds of the type Ph(R)C:C(CN)X(R = Ph or But, X = CN or CO2Et) undergo smooth, efficient, and specific cathodic hydrogenation of the carbon–carbon double bond in aprotic solvents in the presence of added proton donors. For R = But and X = CN, cathodic reduction in the presence of chiral proton donors gives a racemic product which implies that, for established cases of asymmetric electrochemical reduction, protonation is not the stereochemistry-determining step.

Mixtures of stereoisomeric cyclic hydro-dimers are the only products of similar reductions of compounds with R = Me or H and X = CN.

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Article type: Paper
DOI: 10.1039/P19750000971
J. Chem. Soc., Perkin Trans. 1, 1975, 971-974

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    Electro-organic reactions. Part IV. Preparative aspects of the cathodic hydrogenation of activated carbon–carbon double bonds

    L. A. Avaca and J. H. P. Utley, J. Chem. Soc., Perkin Trans. 1, 1975, 971
    DOI: 10.1039/P19750000971

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