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Synthesis of cylclopropanes by reductive cyclization of polychloroalkanes containing a CCl3 OR CCl2 group

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

Conclusions

  1. 1.

    The reductive cyclization of polychloroalkanes of formula RCHClCH2CCl3 (R = H or C6H5) to form cyclopropane compounds is effected by treatment with zinc in ethanol.

  2. 2.

    The formation of chlorinated cyclopropanones by cyclization of polychloroalkanes of the type RCCl2CH2CHClC6H5 (R=Cl or CH3) indicates that the mechanism of reductive cyclizations is the same for compounds with CCl2and CCl3 groups, starting with 1,3-dechlorination.

  3. 3.

    The presence of a\(\begin{array}{*{20}c} \backslash \\ / \\ \end{array} CCl - CCl\begin{array}{*{20}c} / \\ \backslash \\ \end{array} \) fragment in the γ position to the CCl3 group hinders reductive cyclization.

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Authors and Affiliations

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

    R. Kh. Freidlina, A. A. Kamyshova, N. N. Posledova & E. Ts. Chukovskaya

Authors
  1. R. Kh. Freidlina
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  2. A. A. Kamyshova
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  3. N. N. Posledova
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  4. E. Ts. Chukovskaya
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 392–395, February, 1979.

The authors wish to thank L. D. Sychkova for supplying the sample of l-methyl-2-phenylcyclopropane.

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Freidlina, R.K., Kamyshova, A.A., Posledova, N.N. et al. Synthesis of cylclopropanes by reductive cyclization of polychloroalkanes containing a CCl3 OR CCl2 group. Russ Chem Bull 28, 362–365 (1979). https://doi.org/10.1007/BF00925884

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  • DOI: https://doi.org/10.1007/BF00925884

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