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

R. M. Bowman, A. Chambers, W. R. Jackson

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Abstract

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.

Original languageEnglish
Pages (from-to)612-615
Number of pages4
JournalJournal of the Chemical Society C: Organic Chemistry
Publication statusPublished - 1 Dec 1966
Externally publishedYes

Cite this

Bowman, R. M., Chambers, A., & Jackson, W. R. (1966). The epoxidation of p-menth-1- and -3-ene. Journal of the Chemical Society C: Organic Chemistry, 612-615.