The oxidative cleavage of carbon-carbon bonds in 1,2-diols (glycols) is a very important reaction which has frequently been utilized in organic syntheses. Representative oxidants include periodates and lead tetraacetate. Although periodates effectively react with glycols in many cases, the reaction dose not proceed for cyclic trans-glycols and ditertiary glycols. Lead tetraacetate can react with these reactants; and therefore, it has been widely used as a convenient oxidant for glycol cleavage in organic synthesis. However, it is highly toxic, and no less than a stoichiometric amount of reagent is required for the reaction. We found that the reaction of ditertiary glycols in the presence of a catalytic amount of vanadium oxytrichloride under an oxygen atmosphere caused cleavage of carbon-carbon bonds in glycols. This reaction must be an environmentally benign oxidative cleavage of ditertiary glycols.
