Some reactions of copper(I) pentafluorothiophenolate as a nucleophile

Several aromatic compounds containing one or two C₆F₅S groups have been prepared by nucleophilic displacement reactions using CuSC₆F₅ in DMF solution. Aromatic iodine or bromine, rather than chlorine of fluorine is replaced by the SC₆F₅ group using CuSC₆F₅. A mechanism is postulated. New compounds prepared include $\text{p}$-(C₆F₆F₅S)₂C₆H₄, $\text{o}$- and $\text{m}$-(C₆F₅S)₂C₆F₄ and $\text{p}$XC₆H₄SC₆F₅(X=C1, NO₂, I, CH₃, CO₂C₂H₅).     

Reactions of some fluoroaromatics with the ethoxide anion

The reactions of sodium ethoxide in ethanol with various fluoroaromatics, C₆F_6?nH_n, C₆F_5?nH_nNO₂, C₆F₅X (X = CF₃, C₆F₅, COCH₃, CH₂Br), C₆Cl₆ and $\text{m}$H₂C₆Cl₄ have been studied. Partial substitution of the aromatic halogen was observed. The new products have been characterized by elemental analysis, NMR (H?1 and F?19), infrared and mass spectroscopy.     

The thiolate anion as a nucleophile Part XII. Reactions of Lead(II) Benzenethiolate

The reactions of various fluoroaromatics, C₆F_6?xH_x, and C₆F₅X (X = C₆F₆, Cl, Me, NO₂, CF₃, COCl, CH₂Br, OMe, and NH₂) with lead(II) benzenethiolate in DMF have been examined. Lead thiolate acted as an excellent source of benzenethiolate anions and displacement of fluorine, chlorine or the nitro group was observed. The new products have been characterized by elemental analysis, and NMR (H?1 and F?19), infrared and mass spectroscopy.