The thermolysis of α-pinene and verbenone epoxides in supercritical solvents

Abstract

Thermal transformations of α-pinene and verbenone epoxides were studied in supercritical solvents with complex compositions, including CO2, lower alcohols (ethanol and isopropanol), and water, over the temperature and pressure ranges 387–575 K and 135–215 atm. The main product from α-pinene epoxide in a supercritical solvent containing water was campholenic aldehyde and pinocamphone; the total content of these products in the reaction mixture was 80%. Suggestions concerning the mechanism of the thermal isomerization of α-pinene epoxide depending on the acidity of supercritical solvents were made. The direction of verbenone epoxide transformations was independent of the presence of water in the mixture. The main identified products were ketoalcohols with para-menthane and camphane frameworks.