Skip to main content
SpringerLink
Log in

Ionic hydrogenation of alkenyl- and alkylidenecyclopropanes

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

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

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

    Google Scholar 

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

    Google Scholar 

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

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

    Google Scholar 

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

    Google Scholar 

  6. V. A. Slabey and P. H. Wise, J. Am. Chem. Soc.,71, 1518, 3252 (1949).

    Google Scholar 

  7. J. W. Jenkins, N. L. Lavery, P. R. Guenther, and H. W. Post, J. Org. Chem.,13, 862 (1948).

    Google Scholar 

  8. H. D. Hartzler, J. Am. Chem. Soc.,86, 526 (1964).

    Google Scholar 

  9. W. Rahman and H. G. Kuivila, J. Org. Chem.,31, 772 (1966).

    Google Scholar 

  10. G. Schroder, Chem. Ber.,96, 3178 (1963).

    Google Scholar 

Download references

Author information

Authors and Affiliations

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

    Z. N. Parnes, G. A. Khotimskaya, R. V. Kudryavtsev & D. N. Kursanov

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

    Z. N. Parnes, G. A. Khotimskaya, R. V. Kudryavtsev & D. N. Kursanov

Authors
  1. Z. N. Parnes
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. A. Khotimskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. V. Kudryavtsev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. D. N. Kursanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

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

Rights and permissions

Reprints and permissions

About this article

Cite this article

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

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00854486

Keywords

Search

Navigation