Oxidation by the salts of metals. VI. Oxidative iodination of aromatic substrates, promoted by Co(III), Mn(III), and Ce(IV) compounds in aqueous trifluoroacetic acid
The direct iodination of benzene, halogenobenzenes, and p-methoxycarbonyltoluene in trifluoroacetic acid and its aqueous solutions with iodine or alkali-metal iodides was studied in the presence of Co(III) and Mn(III) acetates and ammonium cerium(IV) sulfate, which make it possible to obtain the respective iodoarenes with high yields under mild conditions. In the case of toluene the reaction is complicated by the formation of ..cap alpha..-oxidation products. It is assumed that the iodinating agent is trifluoroacetyl hypoiodite, formed as a result of the oxidation of the iodine by the salt of the metal having variable valence. The highest yields of the iodoarenes were obtained with 90% aqueous trifluoroacetic acid.
- Research Organization:
- Lomonosov Moscow State Univ., Moscow (Russian Federation)
- OSTI ID:
- 6036316
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Vol. 22:6; Other Information: Translated from Zh. Org. Khim.; 22: No.6, 1117-1120(Jun 1986)
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
ACETATES
CATALYTIC EFFECTS
AMMONIUM SULFATES
AROMATICS
IODINATION
OXIDATION
CERIUM SULFATES
CHLORINATED AROMATIC HYDROCARBONS
COBALT COMPLEXES
IODINATED AROMATIC HYDROCARBONS
SYNTHESIS
MANGANESE COMPLEXES
ACETIC ACID
ACTIVATION ENERGY
BENZENE
CHEMICAL REACTION YIELD
CHROMATOGRAPHY
ORGANIC FLUORINE COMPOUNDS
OXIDIZERS
POTASSIUM IODIDES
SODIUM IODIDES
TOLUENE
VALENCE
ALKALI METAL COMPOUNDS
ALKYLATED AROMATICS
AMMONIUM COMPOUNDS
CARBOXYLIC ACID SALTS
CARBOXYLIC ACIDS
CERIUM COMPOUNDS
CHEMICAL REACTIONS
COMPLEXES
ENERGY
HALIDES
HALOGEN COMPOUNDS
HALOGENATED AROMATIC HYDROCARBONS
HALOGENATION
HYDROCARBONS
INORGANIC PHOSPHORS
IODIDES
IODINE COMPOUNDS
MONOCARBOXYLIC ACIDS
ORGANIC ACIDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
OXYGEN COMPOUNDS
PHOSPHORS
POTASSIUM COMPOUNDS
RARE EARTH COMPOUNDS
SEPARATION PROCESSES
SODIUM COMPOUNDS
SULFATES
SULFUR COMPOUNDS
TRANSITION ELEMENT COMPLEXES
YIELDS
400201* - Chemical & Physicochemical Properties