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Study of the reactivity of cyclopropane hydrocarbons by means of deuterium exchange with a solution of potassamide in liquid ammonia

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

Summary

  1. 1.

    Cyclopropane hydrocarbons (ethylcyclopropane, vinylcyclopropane, cyclopropylbenzene), which react fairly readily with acids, are chemically stable, even at 120°, toward such a strong base as a 1 N solution of potassamide in liquid ammonia.

  2. 2.

    Experiments on the isotopic exchange of hydrogen with a solution of potassamide in liquid deuterated ammonia, carried out with isopentane, with ethylcyclobutane, and with ethylcyclopropane, and also a comparison of the rates of deuterium exchange with isopropyl- and cyclopropyl-benzenes, showed that the hydrogen atoms of the three-membered ring have enhanced reactivity.

  3. 3.

    The average rate of deuterium exchange is considerably increased when the three-membered ring is conjugated with a double bond (vinylcyclopropane) or an aromatic ring (cyclopropylbenzene). There is very marked nonequivalence of the hydrogen atoms in these hydrocarbons.

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Authors and Affiliations

  1. L.Ya. Karpov Physicochemical Institute, USSR

    A. I. Shatenshtein, E. A. Yakovleva, M. I. Rikhter, M. Yu. Lukina & B. A. Kazanskii

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

    A. I. Shatenshtein, E. A. Yakovleva, M. I. Rikhter, M. Yu. Lukina & B. A. Kazanskii

Authors
  1. A. I. Shatenshtein
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  2. E. A. Yakovleva
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  3. M. I. Rikhter
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  4. M. Yu. Lukina
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  5. B. A. Kazanskii
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Additional information

The authors thank L.G. Sal'nikova and I.L. Safonova of the Institute of Organic Chemistry of the Academy of Sciences of the USSR for providing some of the hydrocarbons.

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Shatenshtein, A.I., Yakovleva, E.A., Rikhter, M.I. et al. Study of the reactivity of cyclopropane hydrocarbons by means of deuterium exchange with a solution of potassamide in liquid ammonia. Russ Chem Bull 8, 1727–1733 (1959). https://doi.org/10.1007/BF00912109

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  • DOI: https://doi.org/10.1007/BF00912109

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