Journal of Electroanalytical Chemistry, Vol.432, No.1-2, 181-192, 1997
Reduction of Fluoroalkoxyarenes
Fluoroalkoxyarenes can be reduced in liquid ammonia via an irreversible stepwise mechanism. In the case of trifluoromethoxyarenes, the trifluoromethoxyl group behaves as a leaving group and the substrate is reduced into the arene. Conversely, the reduction of a difluoromethoxyarene such as difluoromethoxybenzonitrile does not involve the cleavage of the fluoromethoxyl group but follows the same kind of mechanism as that observed in the reduction of trifluoromethylarenes : the two carbon-fluorine bonds are cleaved at the level of the first reduction wave to yield methoxybenzonitrile.
Keywords:CARBON-OXYGEN BOND;AROMATIC NUCLEOPHILIC-SUBSTITUTION;ELECTROCHEMICAL REDOX CATALYSIS;ELECTRON-TRANSFER;LIQUID-AMMONIA;CLEAVAGE REACTIONS;REACTION PATHWAYS;RADICAL-ANIONS;HALIDES