Reduction of 2, 3-epoxypinane and 3, 4-epoxyc arane

1. In presence of Raney nickel, 2,3-epoxypinane is reduced with formation of two alcohols of composition C10H18O. 2. Hydrogenation is accompanied by the isomerization of 2,3-epoxypinane to a ketone of composition C10H16O, which is identical with the product of the thermal isomerization of the epoxide and with the product of die oxidation of the alcohol C10H18O obtained by the reduction of 2,3-epoxypinane over Raney nickel. 3. The ketone C10H16O, product of the thermal isomerization of 2,3-epoxypinane, is reduced by lithium aluminum hydride to a mixture of two stereoisomeric alcohols of composition C10H18O, which are not identical with the alcohols obtained by the reduction of 2,3-epoxypinane over Raney nickel. 4. When pinocamphone from oil of hyssop is reduced with lithium aluminum hydride, an alcohol C10H18O, which differs from those mentioned above, is formed. 5. In presence of Raney nickel, 3,4-epoxycarane is reduced to an alcohol of composition C10H18O, and under the action of heat it is isomerized to a ketone of composition C10H16O. © 1960 Consultants Bureau Enterprises, Inc