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Issue 0, 1966
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The epoxidation of p-menth-1- and -3-ene


Oxidation of p-menth-3-ene with perbenzoic acid in benzene gives cis- and trans-3,4-epoxymenthane in the ratio ca. 3:2. A similar oxidation of p-menth-1-ene gives cis- and trans-epoxides in the ratio ca. 2:3. The trans-epoxides are more rapidly reduced than the cis-compounds when the mixtures are treated with lithium aluminium hydride; this has been explained in terms of the preferred conformations of the epoxides and the diaxial opening rule. The epoxides from p-menth-1-ene are reduced faster than those from p-menth-3-ene. The stereochemistry of the p-menthan-4-ols has been confirmed.

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J. Chem. Soc. C, 1966, 612-615
Article type

The epoxidation of p-menth-1- and -3-ene

R. M. Bowman, A. Chambers and W. R. Jackson, J. Chem. Soc. C, 1966, 612
DOI: 10.1039/J39660000612

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