B. Shainyan, Yu. S. Danilevich, A. A. Grigor’eva
Nov 1, 2003
Citations
0
Influential Citations
5
Citations
Journal
Russian Journal of Organic Chemistry
Abstract
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.