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Isomerization of the free propyl-d2 radical in solution

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Summary

  1. 1.

    The decomposition of butyryl-2,2-d2 peroxide in boiling carbon tetrachloride was studied.

  2. 2.

    In solution, the propyl radical undergoes isomerization as a result of the migration of a hydrogen atom form the 3-position: CH3-CH2-CD2· ⇌ CH2-CH2-CD2H.

  3. 3.

    A propyl radical labeled with deuterium is isomerized to a smaller extent than a deuterium-free radical.

  4. 4.

    Butyryl-2,2-d2 peroxide decomposes with more difficulty that deuterium-free butyryl peroxide.

  5. 5.

    Some new previously undescribed deuterium-containing compounds were prepared: butyryl-2,2-d2 chloride, butyric-2,2-d2 acid, butyryl-2,2-d2 peroxide, and propyl-1,1-d2 chloride.

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Literature cited

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    O. A. Reutov and T. N. Shatkina, Dokl. AN SSSR,133, 381 (1960).

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    De Los, F. De Tar, and D. V. Wells, J. Amer. Che. Soc.,82, 5839 (1960).

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    A. I. Shatenshtein, Isotopic Analysis of Water [in Russian], Izd. AN SSSR (1958).

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    I. Heilbron and H. M. Bunbury, Dictionary of organic compounds,I, IV. London (1953).

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    T. N. Shatkina, Dissertation [in Russian], Moscow (1962).

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Reutov, O.A., Ostapchuk, G.M. & Remova, V.A. Isomerization of the free propyl-d2 radical in solution. Russ Chem Bull 13, 481–485 (1964). https://doi.org/10.1007/BF00844165

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Keywords

  • Hydrogen
  • Chloride
  • Migration
  • Peroxide
  • Hydrogen Atom