101413-97-2Relevant academic research and scientific papers
FREE-RADICAL REACTIONS OF 1,1,2-TRICHLOROPROPENE. II. FREE-RADICAL THIYLATION OF TRICHLOROPROPENE BY ARENETHIOLS
Martynov, A. V.,Mirskova, A. N.,Vitkovskii, V. Yu.,Voronkov, M. G.
, p. 1056 - 1061 (2007/10/02)
The reaction of CCl2=CClCH3 with ArSH (Ar = 4-ClC6H4, C6H4, 4-CH3C6H4), initiated by UV irradiation, is nonregioselective and nonstereospecific and leads mainly to the formation of mixtures of isomeric sulfides ArSC(CH3)=CCl2 and cis- and trans-ArSCCl=CClCH3.Diaryl disulfides ArSSAr, sulfides ArSCH2CCl=CCl2 and ArSCHClCCl2CH3, and bissulfides cis- and trans-ArSC(CH3)=CClSAr and (ArS)2=CClCH3 are also formed.In the case of 4-ClC6H4SH the thioester ClC6H4SC(O)CCl2CH3 was found.The formation of these products was demonstrated by GLC, IR and PMR spectroscopy, and chromato-mass spectrometry.A reaction mechanism involving the formation of intermediate radicals of ArSC(CH3)ClC.Cl2 and ArSCCl2C.ClCH3 and also the allyl radical .CH2CCl=CCl2 is proposed.
