Organomercury compounds. XIII. The mercuration of 1,2,4,5-tetrafluorobenzene

Abstract

2,3,5,6.Tetrafluorophenylmercuric trifluoroacetate and acetate, 1,4-bis(tri-fluoroacetatomercuri)tetrafluorobenzene, and 1,4-di(acetatomercuri)tetraffuorobenzene have been prepared by mercuration of 1,2,4,5-tetrafluorobenzene with mercuric trifluoroacetate or acetate while 2,3,5,6-tetrafluorophenglmercuric chloride and acetate, 1,4-di(chloromercuri)tetrafluorobenzene, and 1,4-di(acetatomercuri)tetrafluorobenzene have been obtained from the corresponding trifluoroacetates by metathesis reactions. The di(chloromercuri) derivative has also been isolated from reaction of thallous tetrafluoroterephthalate with mercuric chloride. Bis(2,3,5,6-tetrafluorophenyl)mercury has been prepared by rearrangement of 2,3,5,6-tetrafluorophenglmercuric trifluoroacetate with iodide ions, and by mercuration of 1,2,4,5-tetrafluorobenzene with tetrabromomercurate(11) ions under alkaline conditions. The latter reaction also gave a low yield of 1,4-bis(2,3,5,6-tetrafluorophenylmercuri)tetrafluorobenzene, which was identified by N.M.R. spectroscopy, and by degradation with mercuric chloride. The carbon-oxygen stretching frequencies of the new organomercuric carboxylates are indicative of unidentate carboxylate coordination.