- FREE-RADICAL REACTION OF DIARYL DISULFIDES WITH TRI- AND TETRACHLOROETHYLENES
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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.
- Martynov, A. V.,Mirskova, A. N.,Voronkov, M. G.
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- FREE-RADICAL REACTION OF ARENETHIOLS WITH TETRACHLOROETHYLENE
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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.
- Martynov, A. V.,Mirskova, A. N.,Voronkov, M. G.
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p. 1635 - 1640
(2007/10/02)
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