95391-76-7Relevant academic research and scientific papers
CHARACTERISTICS OF THE ADDITION OF ORGANIC DISELENIDES TO THE ETHERATES OF CHLORO- AND DICHLOROACETYLENES
Martynov, A. V.,Mirskova, A. N.,Voronkov, M. G.
, p. 841 - 848 (2007/10/02)
The reaction of diorganic diselenides with chloro- and dichloroacetylenes in diethyl ether leads to the formation of 2-chloro- and 1,2-dichlorovinyl selenides respectively in addition to 1,2-bis(organoseleno)chloro- and 1,2-bis(organoseleno)-1,2-dichloroethylenes.In addition, the appearance of the products from the reaction of diethyl ether with dichloroacetylene and with the diorganic diselenides was observed, i.e., 3-ethoxy-1,2-dichloro-1-butene, bis(1,2-dichloro-1-buten-3-yl) ether, 1-phenylselenodiethyl ether, and 1-alkylseleno-3-ethoxy-1,2-dichloro-1-butenes.In addition to disproportionation of the chloroacetylene, accompanied by the generation of a proton, the reactions leading to the last two compounds are evidently responsible for the appearance of 2-chloro- and 1,2-dichlorovinyl selenides in the reaction mixtures.Arguments are presented in favor of a free-radical mechanism, including the formation of the organoselenyl radical.
CHLOROVINYLATION OF BENZENESELENOL AND ORGANIC DISELENIDES BY CHLORO- AND DICHLOROACETYLENES
Martynov, A. V.,Mirskova, A. N.,Voronkov, M. G.
, p. 1326 - 1328 (2007/10/02)
Mixtures of the Z and E isomers of unsaturated organic selenides and 1,2-bis(organoseleno)mono(di)chloroethylenes were obtained by the addition of benzeneselenol and organic diselenides to the etherates of chloro- and dichloroacetylene
SELENYLATION OF cis- AND trans-1,2-DICHLOROETHYLENES AND VINYLIDENE CHLORIDE UNDER THE CONDITIONS OF PHASE-TRANSFER CATALYSIS
Martynov, A. V.,Mirskova, A. N.,Voronkov, M. G.
, p. 52 - 56 (2007/10/02)
The reaction of PhSeH with cis- and trans-CHCl=CHCl, catalyzed by tributylbenzylammonium chloride, in 36percent 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.
NEW SYNTHESIS OF VINYL SELENIDES NUCLEOPHILIC SUBSTITUTIONS OF UNACTIVATED VINYL HALIDES BY SELENIDE ANIONS
Tiecco, M.,Testaferri, L.,Tingoli, M.,Chianelli, D.,Montanucci, M.
, p. 4975 - 4978 (2007/10/02)
Alkyl and aryl selenide anions react with unactivated vinyl halides, in dipolar aprotic solvents, to give alkyl or aryl vinyl selenides in good yields.These reactions are stereospecific and occur with retention of configuration.
