Synthesis of Novel Diaryl Ether and Thioether Derivatives of Polyfluorochalcones

A series of p-substituted tetrafluoroaldehydes and ketones were obtained by the reaction of pentafluoroacetophenone and pentafluorobenzaldehyde with an excess of 4,4'-thiobisthiophenol, of 4,4'-thiobisphenol, and tert-butylthiophenol. The use of a double excess of pentafluoroacetophenone and pentafluorobenzaldehyde with respect to 4,4'-thiobisthiophenol and of 4,4'-thiobisphenol leads to the formation of bisoctafluoroaldehydes and ketones in high yields. Starting from mono- and disubstituted aldehydes and ketones, novel mono- and bispolyfluorochalcones containing aryl ether and thioether moieties, suitable for further modification, were synthesized.