C [sbnd]F bond activation in the reaction of BiCl 3 with sodium 2,4,6-tris(trifluoromethyl)phenoxide

Abstract

BiCl 3 reacts with sodium 2,4,6-tris(trifluoromethyl)phenoxide (NaOR 4f) in ether solution to produce an unusual condensation product in which three OR f functions have been coupled with the elimination of three fluorine atoms. The product is R fOC 6H 2(CF 3) 2C(O)OR f, which has been characterized spectroscopically and by X-ray crystallography (triclinic space group P 1; a = 8.958(1), b = 12.652(2), c = 13.722(2)Å, α = 89.596(8)°, β = 75.92(1)°, γ = 71.412(7)°, V = 1425.6(3)Å 3, Z = 2). Bi(OR f) 3 is believed to be an intermediate in this process. The carbon fluorine bond activation is not observed in the absence of BiCl 3.