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

Journal Article · Fri Jan 01 04:00:00 EST 1982 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00341a036· OSTI ID:5194043

Wilbur, D S; Anderson, K W

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.

• Research Organization: Los Alamos National Lab., N.M.
• OSTI ID: 5194043
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 47:2; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400300* -- Organic Chemistry-- (-1987)
ALKENES
BROMINATION
BROMINE CHLORIDES
BROMINE COMPOUNDS
CHEMICAL ANALYSIS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
CYCLOALKENES
DATA
EXPERIMENTAL DATA
HALIDES
HALOGEN COMPOUNDS
HALOGENATION
HYDROCARBONS
INFORMATION
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC SOLVENTS
QUANTITATIVE CHEMICAL ANALYSIS
SOLVENTS
STEREOCHEMISTRY
YIELDS