Abstract Optimal conditions were found for induced hydroxyhalogenation of cyclic dienes (tetrahydroindene, 4-vinylcyclohexene and 5-vinyl-and 5-cyclohexenylbicyclo [2.2. 1] hept-2- enes) in the system [MHlg-HA or HHlg]-H 2 O 2 (or NaClO). Dehydrohalogenation of the chloro-and bromohydrins thus obtained with powdered potassium carbonate gave the corresponding diepoxy derivatives, and their hydrolysis led to mixtures of stereoisomeric ...