Sulfonate 7 and

The benzene derivatives containing the fluorinated sulfone have been prepared either by nucleophilic substitution of the 4-fluorophenyl derivative (e.g. 1) or by starting with the appropriately substituted sodium thiophenoxide and reacting with perfluoroalkyl iodide follow by oxidation with either MCPBA or chromium oxide (12. li.) The biphenyl derivatives have been prepared by palladium catalyzed cross coupling chemistry of the 4-bromophenyl derivative (e.g. 2) with substituted phenyl boronic acid (yields 37-84%) (JLH, .). Compound 16 has been prepared by palladium catalyzed cross coupling of (4-bromophenyl)perfluorohexyl sulfone with vinyl anisole in 37 % yield (JJL). The vinyl sulfones, 7 and 9, have been prepared by condensation of CH3S02Rf (JJL) with the appropriate aldehyde (yields 70,and 73%) following a literature procedure (1 ). Yields were not optimized. 

To a solution of 0.40 mmol of sulfone 7 and 0.14 mL (1 mmol, 2.5 equiv)of 70% /-BuOOH in H20 in 3 mL of THF is slowly added at 30 nC, 0.24 mL (0.52 mmol, 1.3 equiv) of a 40% soln of Triton Bin CH3OH. After 2 h, the mixture is diluted with 10 mL of distilled H20 and extracted with three 6-mL portions of EtOAc. Then 142 mg (0.42 mmol, 1.05 equiv) of Bu4N + S04 and 18 mg (0.42 mmol, 1.05 equiv) of LiOH H,0 are added to the aqueous phase followed by extraction with four 10-mL portions of CH2C12. The combined CH2C12 extracts are dried over MgS04 and evaporated to afford the crude epoxides 8. 

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