The preparation and rearrangement of γ-terpineol epoxides

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

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Oxidation of γ-terpineol with perbenzoic acid in benzene gives epoxides in ratio ca. 70 trans to 30 cis. The epoxides have been separated and their stereochemistry established. The epoxides rearrange in aqueous formic acid solution to give a mixture of 8-hydroxy-1,4-cineole (VI) and 4-hydroxy-1,8-cineole (VII). These hydroxy-ethers are the major products when γ-terpineol is oxidised in carbon tetrachloride with perlauric acid.

Original languageEnglish
Pages (from-to)1296-1298
Number of pages3
JournalJournal of the Chemical Society C: Organic
DOIs
Publication statusPublished - 1 Jan 1966
Externally publishedYes

Cite this

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abstract = "Oxidation of γ-terpineol with perbenzoic acid in benzene gives epoxides in ratio ca. 70 trans to 30 cis. The epoxides have been separated and their stereochemistry established. The epoxides rearrange in aqueous formic acid solution to give a mixture of 8-hydroxy-1,4-cineole (VI) and 4-hydroxy-1,8-cineole (VII). These hydroxy-ethers are the major products when γ-terpineol is oxidised in carbon tetrachloride with perlauric acid.",
author = "Bowman, {R. M.} and A. Chambers and Jackson, {W. R.}",
year = "1966",
month = "1",
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doi = "10.1039/J39660001296",
language = "English",
pages = "1296--1298",
journal = "Journal of the Chemical Society C: Organic Chemistry",
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The preparation and rearrangement of γ-terpineol epoxides. / Bowman, R. M.; Chambers, A.; Jackson, W. R.

In: Journal of the Chemical Society C: Organic, 01.01.1966, p. 1296-1298.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - The preparation and rearrangement of γ-terpineol epoxides

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AU - Chambers, A.

AU - Jackson, W. R.

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AB - Oxidation of γ-terpineol with perbenzoic acid in benzene gives epoxides in ratio ca. 70 trans to 30 cis. The epoxides have been separated and their stereochemistry established. The epoxides rearrange in aqueous formic acid solution to give a mixture of 8-hydroxy-1,4-cineole (VI) and 4-hydroxy-1,8-cineole (VII). These hydroxy-ethers are the major products when γ-terpineol is oxidised in carbon tetrachloride with perlauric acid.

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DO - 10.1039/J39660001296

M3 - Article

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JO - Journal of the Chemical Society C: Organic Chemistry

JF - Journal of the Chemical Society C: Organic Chemistry

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