Synthesis of halohydrines of 5-alkylbicyclo[2.2.1]heptene series using the systems inducing electrophilic reagents

Abstract

The reactions of induced hydroxyhalogenation of alkylnorbornenes with the use of a mixture of aqueous solutions of hydrochloric or hydrobromic acids (or sodium, potassium and cobalt bromides) and hydrogen peroxide or sodium hypochloriteare are studied. The reaction are established to proceed through the addition at the double bond of the ring of the electrophilic reagent HOBr or HOCl formed in situ yielding of cis-vicinal halohydrines. By dehydrohalogenation of the latter in the presence of alkali are obtained endo-6-alkyl-endo-3-oxatricyclo[3.2.11.5.02.4]octanes and by their oxidation are synthesized respective haloketones in a high yield.