3559-72-6Relevant academic research and scientific papers
A New Approach to the Synthesis of Symmetrical Bis(organylchalcogeno)acetylenes: Scope and Limitations
Martynov, Alexander V.,Guillanton, Georges Le
, p. 823 - 831 (2007/10/03)
A new general method to prepare bis(organylchalcogeno)acetylenes R-Y-CC-Y-R (Y = S, Se, Te) by dehydrochlorination of the corresponding 1,2-bis(organylchalcogeno)chloroethylenes R-Y-CH=CCl-Y-R with tert-BuOK/tert-BuOH and/or KOH/DMSO is developed.Dechlorination of 1,2-bis(organylchalcogeno)-1,2-dichloroethylenes R-Y-CCl=CCl-Y-R (Y = S, Se, Te) with BuLi in ether or THF is effective only for sulfur derivatives.With Y = Se and alkyl substituents, substitution of the chlorine atom by a butyl group takes place giving rise to 5,6-bis(alkylseleno)dec-5-ene .With aryl substituents, an attack of the ArSe-group by the Bu-radical is observed leading to an aryl butyl selenide.In the case of the tellurium compound Ph-Te-CCl=CCl-Te-Ph, there is a competition between dechlorination to give Ph-Te-CC-Te-Ph, and substitution to produce the phenyl butyl telluride. - Keywords: bis(organylchalcogeno)acetylene; 1,2-bis(organylchalcogeno)chloroethylene; 1,2-bis(organochalcogeno)-1,2-dichloroethylene.
FREE-RADICAL REACTION OF DIARYL DISULFIDES WITH TRI- AND TETRACHLOROETHYLENES
Martynov, A. V.,Mirskova, A. N.,Voronkov, M. G.
, p. 20 - 25 (2007/10/02)
The free-radical reaction of diaryl disulfides ArSSAr with CHCl=CCl2 leads to aryl β,β- and α,β-dichlorovinyl sulfides, trichlorovinyl sulfides, and the trichloroethylene dimer 1,1,3,3,4,4,-hexachloro-1-butene.In the reaction of diaryl disulfides with tetrachloroethylene aryl trichlorovinyl sulfides and hexachloro-1,3-butadiene are formed.A reaction mechanism involving reaction of the vinyl radicals CCl2=C.Cl, CCl2=C.H, adn CHCl-C.Cl with the arylthiyl radical is proposed.
FREE-RADICAL REACTION OF ARENETHIOLS WITH TETRACHLOROETHYLENE
Martynov, A. V.,Mirskova, A. N.,Voronkov, M. G.
, p. 1635 - 1640 (2007/10/02)
The reaction of arenethiols ArSH (Ar = p-Tol, Ph, 4-ClC6H4) with tetrachloroethylene, initiated by UV irradiation or benzoyl peroxide, leads to the formation of mixtures of unsaturated and saturated products, i.e., aryl α,β-dichlorovinyl and β,β-dichlorovinyl sulfides, trichlorovinyl sulfides, 1,1,2,2-tetrachloroethyl and 1,2,2,2-tetrachloroethyl sulfides, diaryl disulfides, and isomeric diarylthiodichloroethenes.During discussion of the reaction mechanism, which involves reaction of the ArS radical with the tetrachloroethylene, evidence is given in favor of an α,β-chlorotropic rearrangement of the intermediate radical ArSCCl2CCl2 to the radical ArSCClCCl3.After the appropriate treatment it is possible to isolate the aryl trichlorovinyl sulfides in a mixture with small amount of aryl α,β-dichlorovinyl and aryl β,β-dichlorovinyl sulfides.
SYNTHESES AND REACTIONS OF PHENYLTHIO AND PROPYLTHIOACETYLENIC COMPOUNDS
Nagashima, Enkou,Suzuki, Kunio,Sekiya, Minoru
, p. 1274 - 1279 (2007/10/02)
Reactions of 2,2-dichlorovinyl sulfides and their sulfoxide and sulfone derivatives with tert-butoxide and with organolithium compounds have provided entries to chloroethynyl sulides, tert-butoxyethynyl sulfides and their derivatives.Application of these reactions for the synthesis of several functional derivatives is also described.Keywords: 2,2-dichlorovinyl sulfide; chloroethynyl sulfide; tert-butoxyethynyl sulfide; ethynyl sulfide; cyclobutenone
FREE-RADICAL CHLOROVINYLATION OF AROMATIC AND ALIPHATIC THIOLS
Mirskova, A. N.,Martynov, A. V.,Voronkov, M. G.
, p. 1766 - 1773 (2007/10/02)
During the free-radical thiylation of trichloroethylene with organic thiols β,β-dichlorovinyl sulfides are formed in a single stage.The reaction of alkanethiols with tetrachloroethylene under analogous conditions leads to trichlorovinyl sulfides.Oxidation of β,β-dichlorovinyl sulfides with hydrogen peroxide in acetic acid leads to the corresponding β,β-dichlorovinyl sulfones.
