The allylic oxidation of a series of alkylated cyclohexenes by selenium dioxide in wet dioxane at high olefin to selenium dioxide ratios has been found to proceed stereoselectively. The conversions of 1, 4-dimethylcyclohexene into 2, 5-dimethylcyclohex-2- en-l-ol and of cis-3, 5-dimethylcyclohexene into 1, 5-dimethylcyclohex-2-en-1-01 both favor the axial alcohol by 70-75%, whereas the conversion of limonene into carveol and trans-A ...
