Stereochemistry of selenium dioxide oxidation of cyclohexenyl systems
EN Trachtenberg, JR Carver
Index: Trachtenberg,E.N.; Carver,J.R. Journal of Organic Chemistry, 1970 , vol. 35, p. 1646 - 1653
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Citation Number: 29
Abstract
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 ...
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