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Ionic hydrogenation of alkenyl- and alkylidenecyclopropanes

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  • 3 Citations

Conclusions

  1. 1.

    A study was made of the ionic hydrogenation of cyclopropane hydrocarbons, containing a double bond in the side chain.

  2. 2.

    On the example of the ionic hydrogenation of the vinyl- and isopropenylcyclopropanes it was shown that the selective hydrogenation of a double bond, conjugated with a three-membered ring, is possible.

  3. 3.

    In the ionic hydrogenation of alkylidenecyclopropane hydrocarbons, and specifically 1,1-dimethyl-2-methylenecyclopropane and 1,1-dimethyl-2-isopropylidenecyclopropane, the selective hydrogenation of the semicyclic double bond fails to occur and the hydrogenation, products are saturated hydrocarbons with an open chain, and specifically 2,3-dimethylbutane and 2,5-dimethylhexane.

  4. 4.

    A reaction scheme was proposed for the ionic hydrogenation of 1,1-dimethyl-2-isopropylidenecyclopropane, which includes the intermediate formation of 2,5-dimethyl-2,4-hexadiene, which compound is capable of taking part in the ionic hydrogenation reaction, both by the 1,2- and by the 1,4-mechanism.

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Literature cited

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    Z. N. Parnes, G. A. Khotimskaya, and M. Yu. Lukina, Dokl. Akad. Nauk SSSR,178, 620 (1968).

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    D. N. Kursanov, Z. N. Parnes, and G. I. Bolestova, Dokl. Akad. Nauk SSSR,181 1132 (1968).

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    Contemporary Problems of Physical Organic Chemistry [in Russian], Mir, Moscow (1967), p. 410.

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    F. A. Carey and H. S. Tremper, J. Am. Chem. Soc.,91, 2967 (1969).

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    Z. N. Parnes, G. A. Khotimskaya, R. V. Kudryatsev, and M. Yu. Lukina, Dokl. Akad. Nauk SSSR,184, 615 (1969).

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 901–905, April, 1972.

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Parnes, Z.N., Khotimskaya, G.A., Kudryavtsev, R.V. et al. Ionic hydrogenation of alkenyl- and alkylidenecyclopropanes. Russ Chem Bull 21, 854–857 (1972). https://doi.org/10.1007/BF00854486

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Keywords

  • Hydrogenation
  • Hydrocarbon
  • Double Bond
  • Vinyl
  • Cyclopropane