Free-radical reactions of halogenated bridged polycyclic compounds. Part XIII. The addition of hydrogen bromide to hexachloromethylenenorbornene

Abstract

The free-radical addition of hydrogen bromide to hexachloromethylenenorbornene affords a 60 : 40 mixture of 1-bromomethyl-2,3,4,5,5,6-endo-hexachloronorborn-2-ene and 5-endo-bromomethyl-1,2,3,4,7,7-hexachloronorborn-2-ene. The aluminium bromide-catalysed ionic addition gives a 68 : 32 mixture of 5-exo-bromo-1,2,3,4,7,7-hexachloro-5-endo-methylnorborn-2-ene and its 5-endo-bromo-epimer.