116525-25-8Relevant articles and documents
PREPARATION OF PHENYL TRIHALOVINYL SELENIDES AND SELENOXIDES
Martynov, A. V.,Mirskova, A. N.
, p. 2106 - 2108 (2007/10/02)
Phenyl trichlorovinyl selenide and phenyl 1,2-dichloro-2-bromovinyl selenide were obtained by the addition of phenylselenenyl chloride and bromide to dichloroacetylene with catalysis by Lewis acids.Hydrogen peroxide oxidation gave the corresponding selenoxides.
REACTION OF BENZENESELENOL WITH TRI- AND TETRACHLOROETHYLENES UNDER CONDITIONS OF PHASE-TRANSFER CATALYSIS
Martynov, A. V.,Mirskova, A. N.,Kalikhman, I. D.,Voronkov, M. G.
, p. 454 - 462 (2007/10/02)
The reaction of benzeneselenol with trichloroethylene in concentrated sodium hydroxide solution, catalyzed by ammonium salts, leads to Z-phenyl α,β-dichlorovinyl selenide with an equimolar ratio of the catalyst and the selenol or to a mixture of the Z and E isomers with a ratio of 1:10.In addition to the expected trichlorovinyl selenide PhSeCCl=CCl2, the analogous reaction with tetrachloroethylene also gives a mixture of the Z and E isomers of α,β-dichlorovinyl selenides and, in addition, 1,2-bis(phenylseleno)-1,2-dichloroethylene PhSeCCl=CClSePh.If trialkylbenzylammonium chlorides R3PhCH2N(1+)*Cl(1-) are used as catalyst, phenyl benzyl selenide PhSeCH2Ph is formed as a side product.The results of the reaction in the case of trichloroethylene are explained by the addition of the selenolate ion to the CClCCl, generated from the trichloroethylene in situ, and isomerization of the initially formed Z-phenyl α,β-dichlorovinyl selenide to the thermodynamically more stable E isomer.In the case of tetrachloroethylene they are explained by the usual addition-elimination mechanism with the formation of trichlorovinyl selenide, accompanied by reductive dechlorination of the CCl2=CCl2 to CHCl=CCl2 by the selenolate and subsequent reaction of the selenolate with CHCl=CCl2.
