Polyfluoroarenes. Part XVII. Some reactions of pentafluorobenzonitrile

Pentafluorobenzonitrile reacts with ammonia, aniline, and o-phenylenediamine and with chloride, bromide, iodide, methoxide, hydroxide, acetate, benzoate, and azide ions mainly by displacement of the 4-fluorine atom. Reaction with an excess of chloride ion yields pentachlorobenzonitrile. Tetrafluoro-4-iodobenzonitrile undergoes attack at the iodine atom itself in the presence of iodide ion, and 4-benzoyloxytetrafluorobenzonitrile yields tetrafluoro-4-hydroxybenzonitrile when it is treated with dimethylformamide. Pentafluorobenzonitrile may be converted into pentafluorobenzaldehyde by reaction with Raney nickel and into pentafluorobenzophenone by reaction with phenylmagnesium bromide.