THE ATTEMPTED SYNTHESIS OF POLYPARATETRAFLUOROPHENYLENE VINYLENE VIA WATER-SOLUBLE AND ORGANIC-SOLVENT SOLUBLE PRECURSOR POLYMERS

2,3,5,6-Tetrafluoro-1,4-xylene-αα′-bis(dimethylsulphonium bromide) (5) and the related -αα′-bis(diethylsulphonium chloride) (6) were prepared by the reaction of αα′-dibromo-2,3,5,6-tetrafluoro-1,4-xylene (7) with dimethyl sulphide and of αα′-dichloro-2,3,5,6-tetrafluoro-1,4-xylene (7a) with diethyl sulphide, respectively. Compound (5) with aqueous alkali was converted into the dibromo compound (7), with no evidence of polymer being formed. Compound (6) failed to give any viable product with aqueous alkali. 2,3,5,6-Tetrafluorobenzene was converted into 1,4-diallyl-2,3,5,6-tetrafluorobenzene (14) via a copper (I) intermediate, and gave 2,3,5,6-tetrafluorobenzene-1,4-diethanal (13) on treatment with ozone. Reaction of 1,4-dilithio-2,3,5,6-tetrafluorobenzene (12) with the dialdehyde (13) failed to give a viable polymer soluble in organic solvents. © 1990.