Conclusions
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1.
A study was made of the homolytic addition of thiophenol to trivinylmethane, 5-chloro-3-vinyl-1-pentene and 5-phenylthio-3-vinyl-1-pentene.
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2.
The initially formed homoallylic radical (CH2=CH)2CHCHCH2SC6H5 is cyclized to the cyclopropylcarbinyl radical\(\begin{gathered} \dot CH_2 - CH - CHCH_2 SC_6 H_5 \hfill \\ \hfill \\ CHCH = CH_2 \hfill \\ \end{gathered} \). These radicals are fixed by reaction with thiophenol, with the formation of 5-phenylthio-3-vinyl-1-pentene and 1-methyl-2-vinyl-3-phenylthiomethylcyclopropane. The latter was identified in the reaction mixture by the PMR method.
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3.
1-Chloro-3-vinyl-5-phenylthiopentane and 3-vinyl-1,5-(bisphenylthio)pentane were respectively obtained by the reaction of 5-chloro-3-vinyl-1-pentene and 5-phenylthio-3-vinyl-1-pentene with thiophenol.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 100–106, January, 1970.
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Vasil'eva, T.T., Fedin, É.I. & Freidlina, R.K. Homolytic addition of thiophenol to trivinylmethane and related compounds. Russ Chem Bull 19, 92–96 (1970). https://doi.org/10.1007/BF00913931
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DOI: https://doi.org/10.1007/BF00913931