93343-12-5Relevant articles and documents
REACTIONS OF AROMATIC COMPOUNDS WITH NUCLEOPHILIC REAGENTS IN LIQUID AMMONIA. REACTION OF POLYFLUORINATED DERIVATIVES OF BENZENE WITH SODIUM AMIDE
Shtark, A. A.,Chuikova, T. V.,Selivanova, G. A.,Shteingarts, V. D.
, p. 2271 - 2276 (2007/10/02)
Under the influence of sodium amide in liquid ammonia at a temperature no higher than -33 deg C pentafluorobenzene, 1,2,4,5-tetrafluorobenzene, and 1,3-difluorobenzene undergo deprotonation with the formation of fluorinated phenyl anions, which are resistant to the elimination of a fluoride ion and can be detected by the formation of the products from interaction with electrophiles (with the initial compound in the first case and with methyl iodide in the other two cases). 1,3,5-Trifluorobenzene behaves similarly in reaction with one equivalent of sodium amide, but with two equivalents of sodium amide this compound and 1,2,3,5-tetrafluorob enzene undergo substitution of a fluorine atom by an amino group with the formation of 3,5-di- and 3,4,5-trifluoroanilines respectively.This is clearly due to the double deprotonation of these compounds with the formation of polyfluorinated m-phenylene dianions, which are then converted with the elimination of a fluoride ion into the corresponding dehydrophenyl anions.