Electrochemical reduction of phenyl(9-m-carboranyl)iodonium tetrafluoroborate

Journal Article · Tue Aug 20 00:00:00 EDT 1985 · Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States)

DOI:https://doi.org/10.1007/BF00951314· OSTI ID:6968109

Groshin, V V; Butin, K P; Shcherbina, T M; Tolstnaya, T P

This paper shows that the controlled-potential electrolysis (-0.4 V, s.c.e.) of phenyl(9-m-carboranyl)iodonium tetrafluoroborate (I) on a mercury cathode in a 0.05 M solution of Bu/sub 4/NBF/sup -//sub 4/ in DMF proceeds regiospecifically with breakage exclusively of the C-I bond in the cation of (I) to give 70% benzene (as indicated in gas-liquid chromatography) and 73% 9-iodo-m-carborane with a current yield of about 80%. These results support a previous hypothesis that all the reactions of phenyl(B-carboranyl)iodonium salts with nucleophiles, which accompany breakage of the C-I bond, proceed by the transfer of one electron from the nucleophile to the iodonium cation.

• Research Organization: A.N. Nesmeyanov Institute of Heteroorganic Compounds, Acad. of Sci., Moscow
• OSTI ID: 6968109
• Journal Information: Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States), Vol. 34:2,PT.2
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
BENZENE
CHEMICAL REACTION YIELD
CARBORANES
ORGANIC BORON COMPOUNDS
ELECTROLYSIS
ORGANIC FLUORINE COMPOUNDS
ORGANIC IODINE COMPOUNDS
BORATES
CHEMICAL BONDS
DISSOCIATION ENERGY
ELECTRON TRANSFER
AROMATICS
BORON COMPOUNDS
CARBON COMPOUNDS
ENERGY
HYDROCARBONS
LYSIS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
OXYGEN COMPOUNDS
YIELDS
400201* - Chemical & Physicochemical Properties
400400 - Electrochemistry