83124-56-5Relevant academic research and scientific papers
REACTIONS OF CHLORINE MONOFLUORIDE. SUBSTITUTION OF CHLORINE ATOMS BY FLUORINE IN CHLORINE-SUBSTITUTED ALKANES AND ESTERS
Chuvatkin, N. N.,Panteleeva, I. Yu.,Boguslavskaya, L. S.
, p. 821 - 827 (2007/10/02)
In anhydrous hydrogen fluoride under mild conditions chlorine monofluoride selectively substitutes the chlorine atoms in chlorine-substituted alkanes and esters by fluorine with the formation of high yields of the corresponding fluorides.The presence of an alkoxycarbonyl group or difluoromethylene group at the α position to the CHCl group deactivates the chlorine atom, and substitution by fluorine does not occur.In chloroalkanes, from which elimination of the chloride ion leads to sufficiently stable carbocations, substitution by fluorine can be realized in the absence of hydrogen fluoride at temperatures between -20 and -60 deg C.The fluorinating capacity of chlorine monofluoride is increased in the presence of catalytic amounts (3-5percent) of antimony pentachloride.Here the reaction is less selective than in hydrogen fluoride.In certain cases substitution is accompanied by hydride transfers.
