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Radical addition of polychloromethanes toα,α-dichlorovinyl compounds

  • Organic and Biological Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

The reaction of CCl4 and CHCl3 with CCl2=CHR, where R=(CH2)3H (I) and (CH2)3Cl (II), gives compounds of type HCCl2CH(CCl3)R, and the adducts HCCl2CH(CCl)2CH2CH2CH2Cl (V) from (I) and HCCl2CH·(CCl3)CH2CH2CHCl2 (VIII) from (II).

From CCl4 and CC12=CHCH2CH2CH=CH2, besides the usual addition product CCl2=CHCH2CH2CHClCH2· CCl3, is formed 1,1-dichloro-2-(trichIoromethyl)-5-(chloromethyl)cyclopentane due to stabilization of the CCl2CH(CCl3)R radical by intramolecular addition to the CH=CH2 group and the subsequent cleavage of chlorine.

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Authors and Affiliations

  1. Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, Moscow

    N. V. Kruglova, Sh. A. Karapet'yan & R. Kh. Freidlina

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  1. N. V. Kruglova
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  2. Sh. A. Karapet'yan
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  3. R. Kh. Freidlina
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1569–1574, July, 1975.

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Kruglova, N.V., Karapet'yan, S.A. & Freidlina, R.K. Radical addition of polychloromethanes toα,α-dichlorovinyl compounds. Russ Chem Bull 24, 1454–1458 (1975). https://doi.org/10.1007/BF00946412

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  • DOI: https://doi.org/10.1007/BF00946412

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