Bromine chloride from N-chlorosuccinimide oxidation of bromide ion. Electrophilic addition reactions in protic and aprotic solvents

Abstract

Bromine chloride can be prepared by condensing chlorine gas into liquid bromine. However, applications of this method of bromine chloride formation to millimolar or smaller scale reactions is limited because of the difficulty in quantitating the amounts of each halide added. Bromine chloride may presumably be formed more conveniently from the reaction of compounds containing electrophilic halogens (Br/sup +/ or Cl/sup +/) and the appropriate halide ion. Surprisingly, very few investigations of this method of bromine chloride formation have been reported in the literature. A desire to explore methods of generating electrophilic brominating agents in situ led to an investigation of the formation of bromine chloride from N-chlorosuccinimide (NCS) and bromide ion. We now report on the reaction products obtained from the reaction of cyclohexene with what appears to be bromine chloride formed from NCS and lithium bromide in a variety of solvents.