KF ADSORBED ON ALUMINA EFFECTIVELY PROMOTES THE EPOXIDATION OF ELECTRON-DEFICIENT ALKENES BY ANHYDROUS T-BUOOH

KF adsorbed on alumina (KF-Al2O3) has been studied in detail for the e poxidation of electron deficient alkenes with anhydrous t-BuOOH. Aqueo us base sensitive functional groups survive the reagent Cyclopentenone s are oxidized in decent to quantitative yields without showing any ob servable aldol products. alpha,beta,gamma,delta-Dienones are regiosele ctively oxidized at the alpha,beta-position. Unlike aqueous alkaline H 2O2, KF-Al2O3 is non-stereospecific and offers a mixture of cis and tr ans oxides from most acyclic enones. Except for the oxidation of alpha ,beta-unsaturated lactones and for the difference in reaction rates, t he present reagent is, in general, similar to the t-BuOOH-DBU combinat ion.