Free-radical reactions of halogenated bridged polycyclic compounds. Part XVII. Reaction of 5-alkyl-1,2,3,4,7,7-hexachloronorborna-2,5-dienes and 5-alkenyl-1,2,3,4,7,7-hexachloronorborn-2-enes with N-bromosuccinimide

Abstract

5-Alkyl-1,2,3,4,7,7-hexachloronorborna-2,5-dienes react with N-bromosuccinimide in refluxing carbon tetrachloride to form allylic bromides in a process in which the 5,6-double bond migrates to become exocyclic to the ring system. Products from the corresponding 5-alk-1-enylhexachloronorbornenes are identical. 5-(1-Methylalk-1-enyl)hexachloronorbornenes react to form allylic bromides in which the position of the double bond is unchanged, but in which C-3 of the side chain prefers to be trans rather than cis to the norbornene ring system.