Selenylation of cis- and trans-1,2-dichloroethylenes and vinylidene chloride under the conditions of phase-transfer catalysis

The reaction of PhSeH with cis- and trans-CHCl=CHCl, catalyzed by tributylbenzylammonium chloride, in 36% sodium hydroxide solution with and without the presence of diethyl ether gives cis-PhSeCH=CHCl. The reaction also leads to the formation of trans-PhSeCH=CHCl and PhSeCCl=CH2 in small amounts, depending on the type of dichloroethylene and the presence of diethyl ether. Phenyl benzyl selenide is a side product for all the dichloroethylene isomers. The formation of the isomeric selenides was explained by the trans- and cis-addition of the selenol to the in situ generated chloroacetylene