1-(Trifluoromethyl)ethenyl Phenyl Selenide and 1-(Trifluoromethyl)ethenyl Phenyl Sulfide

Article abstract of DOI:10.1021/jo01298a041

The title compounds were prepared by addition of phenylselenenyl chloride or phenylsulfenyl chloride to 3,3,3-trifluoropropene, followed by elimination of HCl.Both compounds react readily with nucleophiles, giving with ethyl acetoacetate novel 2-fluoro-4H-pyran derivatives.The selenium-substituted olefin reacted with n-butyllithium at selenium to give phenyl n-butyl selenide, while the corresponding sulfur-containig species underwent exclusive attack at the methylene terminus of the olefin.