Oxidation by cobalt(III) acetate. Part 12. Stereoselective formation of threo-1-phenylpropane-1,2-diol monoacetate in oxidation of β-methylstyrenes unsubstituted and substituted with electron-donating groups by cobalt(III) and manganese(III) acetate in acetic acid

Abstract

Stereochemistry in oxidation of β-methylstyrenes unsubstituted and substituted with electrondonating groups (H, p-MeO, and p-Me) by cobalt(III) and manganese(III) acetate in acetic acid or in acetic acid containing trifluoroacetic acid has been studied. threo-1-Aryl propane-1,2-diol monoacetates were the main products in the oxidations of both E- and Z-alkenes by these oxidants. These results are explained in terms of the difference in stabilities between intermediate (11) and (14).