The preparation and rearrangement of γ-terpineol epoxides

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

doi:10.1039/J39660001296

The preparation and rearrangement of γ-terpineol epoxides

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

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6 Citations (Scopus)

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 language	English
Pages (from-to)	1296-1298
Number of pages	3
Journal	Journal of the Chemical Society C: Organic Chemistry
DOIs	https://doi.org/10.1039/J39660001296
Publication status	Published - 1 Jan 1966
Externally published	Yes

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AU - Jackson, W. R.

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N2 - 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.

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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JO - Journal of the Chemical Society C: Organic Chemistry

JF - Journal of the Chemical Society C: Organic Chemistry

ER -

The preparation and rearrangement of γ-terpineol epoxides

Abstract

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