The interaction of polyfluorinated bis(fluorosulfato)carbonyl compounds with nucleophiles

Abstract

The action of LiCl or LiBr on polyfluorinated bis(fluorosulfato)- carbonyl compounds leads to substitution of one FSO 3-group, predominatingly in α-position and simultaneous formation of second carbonyl function: ▪ (I,II) R=(CF 3) 2CF;Z(I)=OCH 3;Z(II)=C 2F 5; Hal=Cl,Br Depending on reaction condition(I) interacts with CsF to formate diketoester(III) or epoxide (IV); ketone (II) is transformed into the mixture of isomeric ketones (V–VI). In DMF media(II) gives oxirane (VII),which dimerizes in the cours of reaction. Triketone (VIII) was obtained by reaction of (II) with MeOH and subsequent make up with H 2S0 4. ▪