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Oxidation by the salts of metals. III. Oxidative halogenation of toluene by alkali-metal chlorides and bromides, promoted by the salts of trivalent cobalt and manganese in trifluoroacetic acid and its aqueous solutions

Journal Article · · J. Org. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:6286411
; ;
The oxidation of toluene by the stoichiometric amounts of cobalt(III) and manganese(III) acetates (C/sub 6/H/sub 5/CH/sub 3/:M/sup 3 +/ = 0.5) in the presence of alkali-metal chlorides and bromides (M/sup 3 +/:Hlg/sup -/ = 1-2) in trifluoroacetic acid and its aqueous solutions (5-50 vol. % of water) was investigated. The main reaction products are halogenotoluenes, benzyl halides, and benzyl trifluoroacetates. The distribution of the reaction products depends largely both on the nature of the oxidizing agent and halide ion and on the water content of the reaction system. Conditions were found for the preparative synthesis of bromotoluenes (in the system Br/sup -/:M/sup 3 +/ = 1.5, CF/sub 3/COOH:H/sub 2/O = 9:1-1:1) and benzyl chloride (Cl/sup -/:M/sup 3 +/ = 1.5, CF/sub 3/COOH:H/sub 2/O = 4:1). Possible mechanisms of oxidative halogenation under the investigated conditions are discussed.
Research Organization:
M.V. Lomonosov Moscow State Univ., USSR
OSTI ID:
6286411
Journal Information:
J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 21:8; ISSN JOCYA
Country of Publication:
United States
Language:
English

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACETATES
ALKALI METAL COMPOUNDS
ALKYLATED AROMATICS
AQUEOUS SOLUTIONS
AROMATICS
BROMIDES
BROMINATED AROMATIC HYDROCARBONS
BROMINATION
BROMINE COMPOUNDS
CARBOXYLIC ACID SALTS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHLORIDES
CHLORINATED AROMATIC HYDROCARBONS
CHLORINATION
CHLORINE COMPOUNDS
CHROMATOGRAPHY
COBALT COMPLEXES
COMPLEXES
DISPERSIONS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED AROMATIC HYDROCARBONS
HALOGENATION
HYDROCARBONS
KINETICS
LITHIUM CHLORIDES
LITHIUM COMPOUNDS
LITHIUM HALIDES
MANGANESE COMPLEXES
MASS SPECTRA
MIXTURES
ORGANIC BROMINE COMPOUNDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
OXIDATION
REACTION KINETICS
SEPARATION PROCESSES
SODIUM BROMIDES
SODIUM COMPOUNDS
SOLUTIONS
SPECTRA
TOLUENE
TRANSITION ELEMENT COMPLEXES
VALENCE
YIELDS