1-[HYDROXY(SULFONYLOXY)IODO]1H,1H-PERFLUOROALKANES - STABLE, FLUOROALKYL ANALOGS OF KOSERS REAGENT

-[Hydroxy(sulfonyloxy)iodo]-1H,1H-perfluoroalkanes 3 [R(f)CH(2)I(OH)OS P(2)R; R = CH3, CF3, p-CH3C6H4, R(f) = CF3, C2F5] can be prepared in t wo steps from the appropriate iodofluoroalkanes by oxidation with pero xytrifluoroacetic acid and subsequent reaction with TsOH, MsOH, or Me( 3)SiOTf. The tosylate derivative 3a reacts with silyl enol ethers unde r mild conditions to give the respective alpha-(tosyloxy) ketones. A s imilar reaction of cyclohexene furnishes cis-1,2-bis(tosyloxy)cyclohex ane as the major product. Triflates 3c,f react with (trimethylsilyl)ar enes under mild conditions to afford the respective (fluoroalkyl) (ary l)iodonium triflates 7, while the analogous reaction with alkynyltrime thylsilanes leads to novel (fluoroalkyl)(alkynyl)iodonium salts 8.