Oxidation by metal salts. V. Oxidative halogenation of benzene and halobenzenes promoted by Co(III) and Mn(III) acetates in trifluoroacetic acid and its aqueous solutions (in Russian)
Journal Article
·
· J. Org. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:6136961
A study was carried out on the oxidation of benzene and halobenzenes by Co(III) and Mn(III) acetates in the presence of alkali metal chlorides and bromides in CF/sub 3/CO/sub 2/H and its aqueous solutions (10-33 vol. % H/sub 2/O). The optimal water content in the solution is a function both of the nature of the metal oxidizing agent and the aromatic substrate. The reaction presumably proceeds through the formation of an aromatic radical-cation which then reacts with the halide anion. The oxidative chlorination of bromobenzene is complicated by ipso substitution and bromine redistribution. Phenyl iodosodichloride may be isolated in preparative yield in the chlorination of iodobenzene. In other cases, variation of the reaction conditions may give high yields of the corresponding chlorine and bromine derivatives. The feasibility of polychlorination was studied. Possible reaction mechanisms were considered.
- Research Organization:
- M. V. Lomonosov Moscow State Univ., USSR
- OSTI ID:
- 6136961
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 22:4; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- Russian
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACETATES
AROMATICS
BENZENE
BINDING ENERGY
BROMINATED AROMATIC HYDROCARBONS
BROMINATION
CARBOXYLIC ACID SALTS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHLORINATED AROMATIC HYDROCARBONS
CHLORINATION
CHROMATOGRAPHY
COBALT COMPLEXES
COMPLEXES
ENERGY
HALOGENATED AROMATIC HYDROCARBONS
HALOGENATION
HYDRATES
HYDROCARBONS
IODINATED AROMATIC HYDROCARBONS
KINETICS
MANGANESE COMPLEXES
ORGANIC BROMINE COMPOUNDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
OXIDATION
OXIDIZERS
REACTION KINETICS
REDOX POTENTIAL
SEPARATION PROCESSES
STRUCTURAL CHEMICAL ANALYSIS
TRANSITION ELEMENT COMPLEXES
VALENCE
YIELDS
400201* -- Chemical & Physicochemical Properties
ACETATES
AROMATICS
BENZENE
BINDING ENERGY
BROMINATED AROMATIC HYDROCARBONS
BROMINATION
CARBOXYLIC ACID SALTS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHLORINATED AROMATIC HYDROCARBONS
CHLORINATION
CHROMATOGRAPHY
COBALT COMPLEXES
COMPLEXES
ENERGY
HALOGENATED AROMATIC HYDROCARBONS
HALOGENATION
HYDRATES
HYDROCARBONS
IODINATED AROMATIC HYDROCARBONS
KINETICS
MANGANESE COMPLEXES
ORGANIC BROMINE COMPOUNDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
OXIDATION
OXIDIZERS
REACTION KINETICS
REDOX POTENTIAL
SEPARATION PROCESSES
STRUCTURAL CHEMICAL ANALYSIS
TRANSITION ELEMENT COMPLEXES
VALENCE
YIELDS