Reactions of alkynylselenonium salts with tetrabutylammonium halides: Apparent umpolung of alkynyl moiety

Article abstract of DOI:10.1016/S0040-4039(98)02492-7

The reactions of alkynylselenonium salts with n-Bu₄NX (X = I, Br, Cl) in CH₂Cl₂ gave 1-halo-1-alkynes or phenacyl halide derivatives and selenide, while the reaction with F afforded a terminal alkyne and a selenoxide. Seemingly, the selenonium salts acted as alkynyl cations in the former case and as alkynyl anions in the latter case.