Organomercury compounds

The tetrafluorophenylmercuric trifluoroacetates, RHgO 2 CCF 3 (R = o -HC 6 F 4 , m -HC 6 F 4 , p -MeOC 6 F 4 , or o -O 2 NC 6 F 4 ), and the dimercurated tetrafluorobenzenes o -(CF 3 CO 2 Hg) 2 C 6 F 4 and m -(CF 3 CO 2 Hg) 2 C 6 F 4 have been prepared by mercuration of the appropriate tetrafluorobenzenes with mercuric trifluoroacetate. Reaction of 1,2,3,4-tetrafluorobenzene with mercuric acetate did not give pure monomercurated or dimercurated products, but o -HC 6 F 4 HgO 2 CCH 3 and o -(CH 3 CO 2 Hg) 2 C 6 F 4 were obtained analytically pure by treatment of the appropriate trifluoroacetates with acetic acid. The diarylmercurials R 2 Hg (R = o -HC 6 F 4 , m -HC 6 F 4 , p -MeOC 6 F 4 , or o -O 2 NC 6 F 4 ) were prepared by symmetrization of the tetrafluorophenylmercuric trifluoroacetates with iodide or bromide ions in methanol or aqueous methanol. A good yield of ( p -MeOC 6 F 4 ) 2 Hg, and low yields of crude ( m -HC 6 F 4 ) 2 Hg and ( o -O 2 NC 6 F 4 ) 2 Hg were obtained by mercuration of the corresponding tetrafluorobenzenes under basic conditions, but ( o -HC 6 F 4 ) 2 Hg could not be obtained by this method. The halogeno derivatives RHgX (R = o -HC 6 F 4 or m -HC 6 F 4 ), o -(XHg) 2 C 6 F 4 , and m -(XHg) 2 C 6 F 4 (X = Cl or Br) have been synthesized from the appropriate trifluoroacetates and hydrogen halides and/or by redistribution reactions of suitable mercurials and mercuric halides.