HYDROGENOLYSE EN PHASE LIQUIDE SUR Pd/C DES EPOXYDES DU CARVOMENTHENE ET DU LIMONENE

Article abstract of DOI:10.1016/S0040-4020(01)98846-5

Hydrogenolysis over Pd/C of cis and trans epoxides of carvomenthene and limonene give a mixture of hydrocarbons, secondary and tertiary alcohols, and ketones in proportions dependent upon the nature of the starting material.In the limonene epoxides, the extracyclic double bond plays an important role in the opening of the oxirane ring through a common unsaturated tertiary alcohol intermediate by double bond migration, hydrogenation of which leads to the products.For the carvomenthene epoxides the results are similar to those found in the 4-t-butyl series with competition between cis addition and trans addition of hydrogen.The presence of the isopropenyl group leads to slower reaction rates in comparison with t-butyl analogues.