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Issue 5, 1977
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Stereoselectivity in the epoxidation of βγ-unsaturated carboxylic acids

Abstract

Epoxidation of the βγ-unsaturated acids (VII)–(IX) by peroxy-acids over a range of reaction conditions has been investigated. In non-basic solvents there is a significant tendency for preferential epoxidation cis to carboxy-group, which is more marked for (IX) with pseudoaxial CO2H. This preference, which disappears in more basic solvents, is explained in terms of H-bonding between CO2H and peroxy-acid in the transition state (XVI).

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Article type: Paper
DOI: 10.1039/P19770000572
Citation: J. Chem. Soc., Perkin Trans. 1, 1977,0, 572-575
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    Stereoselectivity in the epoxidation of βγ-unsaturated carboxylic acids

    S. G. Davies and G. H. Whitham, J. Chem. Soc., Perkin Trans. 1, 1977, 0, 572
    DOI: 10.1039/P19770000572

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