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

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

Research output: Contribution to journalArticleResearchpeer-review

11 Citations (Scopus)

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
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, 612-615.
Bowman, R. M. ; Chambers, A. ; Jackson, W. R. / The epoxidation of p-menth-1- and -3-ene. In: Journal of the Chemical Society C: Organic. 1966 ; pp. 612-615.
@article{a5f3219a27a748c68c018209d76b4d6f,
title = "The epoxidation of p-menth-1- and -3-ene",
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.",
author = "Bowman, {R. M.} and A. Chambers and Jackson, {W. R.}",
year = "1966",
month = "12",
day = "1",
language = "English",
pages = "612--615",
journal = "Journal of the Chemical Society C: Organic Chemistry",
issn = "0022-4952",
publisher = "The Royal Society of Chemistry",

}

Bowman, RM, Chambers, A & Jackson, WR 1966, 'The epoxidation of p-menth-1- and -3-ene', Journal of the Chemical Society C: Organic, pp. 612-615.

The epoxidation of p-menth-1- and -3-ene. / Bowman, R. M.; Chambers, A.; Jackson, W. R.

In: Journal of the Chemical Society C: Organic, 01.12.1966, p. 612-615.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - The epoxidation of p-menth-1- and -3-ene

AU - Bowman, R. M.

AU - Chambers, A.

AU - Jackson, W. R.

PY - 1966/12/1

Y1 - 1966/12/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=37049127830&partnerID=8YFLogxK

M3 - Article

SP - 612

EP - 615

JO - Journal of the Chemical Society C: Organic Chemistry

JF - Journal of the Chemical Society C: Organic Chemistry

SN - 0022-4952

ER -

Bowman RM, Chambers A, Jackson WR. The epoxidation of p-menth-1- and -3-ene. Journal of the Chemical Society C: Organic. 1966 Dec 1;612-615.