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Ionic hydrogenation of bicyclic hydrocarbons containing a three-membered ring

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

Conclusions

  1. 1.

    Bicyclo[3.1.0]hexane, bicyclo[4.1.0]heptane, 1-methylbicyclo[3.1.0]hexane, and 1-methylbicyclo[4.1.0]heptane enter into the ionic hydrogenation reaction with the formation of substituted cycloalkanes.

  2. 2.

    The ionic hydrogenation of 1-methylbicyclo[3.1.0]hexane proceeds stereoselectively with the predominant formation of trans-1,2-dimethylcyclopentane. The predominance of trans-1,2-dimethylcyclohexane is slight in the hydrogenation of 1-methylbicyclo[4.1.0]heptane.

  3. 3.

    The insertion of an angular methyl group into the molecule of bicycloalkanes greatly accelerates the ionic hydrogenation rate.

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Authors and Affiliations

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

    G. A. Khotimskaya, R. V. Kudryavtsev, E. M. Mil'vitskaya, A. F. Plate & Z. N. Parnes

  2. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, USSR

    G. A. Khotimskaya, R. V. Kudryavtsev, E. M. Mil'vitskaya, A. F. Plate & Z. N. Parnes

  3. M. V. Lomonosov Moscow State University, Moscow

    G. A. Khotimskaya, R. V. Kudryavtsev, E. M. Mil'vitskaya, A. F. Plate & Z. N. Parnes

Authors
  1. G. A. Khotimskaya
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  2. R. V. Kudryavtsev
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  3. E. M. Mil'vitskaya
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  4. A. F. Plate
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  5. Z. N. Parnes
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 1989–1992, September, 1972.

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Khotimskaya, G.A., Kudryavtsev, R.V., Mil'vitskaya, E.M. et al. Ionic hydrogenation of bicyclic hydrocarbons containing a three-membered ring. Russ Chem Bull 21, 1930–1933 (1972). https://doi.org/10.1007/BF00854608

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  • DOI: https://doi.org/10.1007/BF00854608

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