REARRANGEMENT OF ALLYLIC AND PROPARGYLIC ALCOHOLS CATALYZED BY THE COMBINED USE OF TETRABUTYLAMMONIUM PERRHENATE(VII) AND PARA-TOLUENESULFONIC ACID

Allylic rearrangement and/or dehydration reaction of allylic alcohols proceeds smoothly by the use of catalytic amounts of tetrabutylammonium perrhenate and p-toluenesulfonic acid hydrate. Treatment of propargylic alcohols with the catalysts at room temperature affords the rearranged products, alpha,beta-unsaturated carbonyl compounds, while beta,gamma-unsaturated ketones are obtained as main products by the reaction in refluxing 1,2-dichloroethane. The application of this catalytic system is also described for the preparation of some synthetic intermediates.