Synthesis and chemical properties of Di(2-fluoro-2-polyfluoroalkyl- alkenyl)sulfides and 2,6-bis(polyfluoroalkyl)-1,4-oxathiine 4,4-dioxides

摘要

Di(1,1-dihydropolyfluoroalkyl)sulfides were synthesized by alkylation of sodium sulfide with tosylates or triflates of the corresponding 1,1-dihydropolyfluoroalkanoles. Dehydrofluorination of the obtained sulfides with strong organic bases such as alkylimino tris(dialkylamino) phosphoranes results in the formation of E-isomers of di(2-fluoro-2-polyfluoroalkyl alkenyl)sulfides. Oxidation of di(1,1-polyfluoroalkyl)sulfides by hydrogen peroxide in acetic acid affords di(1,1-polyfluoroalkyl)sulfones, dehydrofluorination of these compounds under the action of triethylamine allowed access to the E-isomers of di(2-fluoro-2-polyfluoroalkyl-alkenyl)sulfones. The obtained sulfones are convenient starting compounds for the synthesis of previously unknown fluorine-containing derivatives of monocyclic oxathiines.