REDUCTION OF EPOXIDES .3. LITHIUM ALUMINUM HYDRIDE AND MIXED HYDRIDE REDUCTION OF SOME SECONDARY-TERTIARY EPOXIDES

The lithium aluminum hydride (LAH) and mixed LAH-aluminum chloride reductions of the epoxides of 1-methylcyclohexene, 1,2-dimethylcyclohexene, 1,4-dimethylcyclohexene, 1 -methyl-4-t-butylcyclohexene, and trans-2-methyl-∆2-octalin in ether have been examined. In certain cases considerable product control is possible through choice of reagent. Energy parameters have been determined for the various factors which control the direction of opening of substituted cyclohexene oxides, i.e., secondary vs. tertiary hydride attack, chair vs. twist transition state, and contributions from alternate half-chair epoxide conformations. © 1969, American Chemical Society. All rights reserved.