Electrochemical Fluorination of Benzamide and Acetanilide in Anhydrous HF and in Acetonitrile.

Autor: Shainyan, B. A., Danilevich, Yu. S., Grigor'eva, A. A., Chuvashev, Yu. A.
Předmět:
Zdroj: Russian Journal of Organic Chemistry; Apr2004, Vol. 40 Issue 4, p513-517, 5p
Abstrakt: Electrochemical fluorination of benzamide in anhydrous hydrogen fluoride does not involve the amide group but occurs exclusively at the aromatic ring, yielding isomeric fluoro- and difluorobenzamides and 3,3,6,6-tetrafluoro-1,4-cyclohexadienecarboxamide. Electrochemical fluorination of benzamide in acetonitrile as solvent gives the same products, as well as benzonitrile and its fluorinated derivatives and products of hydrolysis and fluorination of acetonitrile. Electrochemical fluorination of acetanilide in anhydrous HF leads to complete tarring of the reaction mixture, while its fluorination in acetonitrile results in selective formation of m-fluoroacetanilide. [ABSTRACT FROM AUTHOR]
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