SCHEDULED MAINTENANCE
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.
R. M. Bowman, A. Chambers and W. R. Jackson, J. Chem. Soc. C, 1966, 1296 DOI: 10.1039/J39660001296
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