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Reductive cyclization of compounds with a CCl2CH2CCl(CH3)2 grouping

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    1,1,2-Trimethylcyclopropane (46%) and 1-chloro-1,2,2-trimethylcyclopropane (13%) were obtained from 2,2,4-trichloro-4-methylpentane, while 1-(β-chloroethyl)-2,2-dimethylcyclopropane (18%), 1-chloro-1-(β-chloroethyl)-2,2-dimethylcyclopropane (16%), and isobutylidenecyclopropane (25%) were obtained from 1,3,3,5-tetrachloro-5-methylhexane. As a result, it was shown that a chlorine atom, attached to a tertiary C atom, is involved in reductive cyclization.

  2. 2.

    It was shown for the first time that the process has a stepwise course: 1,3-dechlorination occurs initially, which leads to the formation of chlorocyclopropanes. Then the chlorine atom in the chlorocyclopropane is either replaced by hydrogen or else it is dehydrochlorinated to a cyclopropane with an exocyclic multiple bond.

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Literature cited

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Authors and Affiliations

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

    A. A. Kamyshova, S. D. Polishchuk, E. Ts. Chukovskaya & R. Kh. Freidlina

Authors
  1. A. A. Kamyshova
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  2. S. D. Polishchuk
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  3. E. Ts. Chukovskaya
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  4. R. Kh. Freidlina
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 185–189, January, 1977.

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Kamyshova, A.A., Polishchuk, S.D., Chukovskaya, E.T. et al. Reductive cyclization of compounds with a CCl2CH2CCl(CH3)2 grouping. Russ Chem Bull 26, 160–164 (1977). https://doi.org/10.1007/BF00921519

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  • DOI: https://doi.org/10.1007/BF00921519

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