Selective Electrochemical Aromatic Fluorination of Acetophenone and Benzophenone.

Autor: Shainyan, B. A., Danilevich, Yu. S., Grigor'eva, A. A., Chuvashev, Yu. A.
Předmět:
Zdroj: Russian Journal of Organic Chemistry; Nov2003, Vol. 39 Issue 11, p1581-1586, 6p
Abstrakt: Electrochemical fluorination of acetofenone and benzophenone was studied in anhydrous HF and in solutions. The electrochemical fluorination of acetophenone in HF occurred exclusively in the ring and furnished ortho- and meta-isomers of fluoroacetophenone, 2,5-difluoroacetophenone, and 1-(3,3,6,6-tetrafluoro-1,4-cyclohexadienyl)-1-ethanone. The fluorination of benzophenone in anhydrous HF furnished predominantly m-fluorobenzophenone, whereas in the presence of chloroform only chlorination products were obtained. The electrochemical fluorination of acetophenone in acetonitrile gave rise only to mono- and difluorinated products. The reasons for readily occurring oxidative fluorination of aromatic compounds into polyfluoro-1,4-cyclohexadienes were discussed, and the decomposition paths of fluorinated products under electron impact were considered. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index