Polyfluorocarbanion chemistry. Part III. Reaction of hexafluoropropene with pentafluorobenzonitrile

Abstract

Hexafluoropropene reacts with pentafluorobenzonitrile in the presence of caesium fluoride to give two mono-(2- and 4-), two di-(2,4- and 2,5-), and two tri-(2,4,5- and 2,4,6-)(perfluoroisopropyl) derivatives; no solvent is necessary. The 2,4,5-derivative rearranges to the less sterically hindered 2,4,6-derivative when heated with fluoride ion. The ring fluorine atoms in the perfluoroisopropyl derivatives are highly susceptible to nucleophilic displacement; the cyano-group resists hydrolysis.