The preparation and rearrangement of γ-terpineol epoxides

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

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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 Chemistry
Publication statusPublished - 1 Jan 1966
Externally publishedYes

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