SYNTHESIS OF FLUORINATED VINYL SULFIDES AND SELENIDES

Article abstract of DOI:10.1016/S0040-4020(01)90306-0

The reaction between fluoroolefins 1 and 10e and benzenesulfenyl or selenenyl halides 6 is found to be solvent-dependent and gives in most cases predominantly the regioisomer 8.The structure of adducts 8 and 9 are ascertained by ¹H, ¹⁹F and ⁷⁷Se NMR spectroscopy.Compounds 8 are easily halogenated and treatment of the products with magnesium or zinc leads to the desired polyfluorovinyl sulfides and selenides 10.A second route of synthesis of these reagents results from the reaction of fluorovinyllithio-derivatives 11 with benzenesulfenyl or selenenyl halides.Olefin 10e is also obtained from the selenoacetal 8t of trifluoroacetaldehyde.