Skip to main content
SpringerLink
Log in

Exchange of hydrogen atoms of saturated cyclic hydrocarbons with sulfuric acid

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

Summary

  1. 1.

    A study has been made of the hydrogen-exchange reaction occurring when heavy sulfuric acid reacts with saturated cyclic hydrocarbons(cyclohexane, methylcyclohexane, 1,1-dimethyleyclohexane, 1,4-dimethylcyelohexane, 1-ethyl-4-merhylcyclohexane, eyclopentane, methylcyclopentane, and cis- and trans -decahydronaphthalenes).

  2. 2.

    It has been established that monocyclic hydrocarbons containing tertiary carbon atoms (methylcyclohexane, 1,4-d:methyloyclohexane, 1-ethyl-4-methylcyclohexane, and methylcyclopentane) undergo hydrogen exchange, equilibrium being established in a few hours at room temperature.

  3. 3.

    It has been Found that no hydrogen exchange is to be observed between heavy sulfuric acid and cis- and trans-decahydronaphthalenes,

  4. 4.

    It has been established that, when a mixture of a hydrocarbon containing a tertiary carbon atom with a hydrocarbon that does not contain a tertiary carbon atom is treated with heavy sulfuric acid, only the hydrocarbon containing the tertiary carbon atom takes part in hydrogen exchange.

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. D. N. Kursanov, V. N. Setkina, and O. D. Sterligov, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1953, No. 6, 1035.

  2. V. N. Setkina, D. N. Kursanov, and O. D. Sterligov, Proc. Acad. Sci. USSR, 85, 1045 (1952).

    Google Scholar 

  3. A. L. Liberman and B. A. Kazansky, Bull. Acad. Sci, USSR, Div. Chem. ,Sci., 1946, No. 1, 77,

  4. B. A. Kazansky, E. M. Terentyeva, and T. F. Bulanova, Syntheses of Organic Compounds, Acad. Sci. USSR Press, Moscow, 1950, p. 161.

    Google Scholar 

  5. N. D. Zelinsky and Yu. A. Arbuzov, Proc. Acad. Sci., USSR, 23, 793 (1939).

    Google Scholar 

  6. N. D. Zelinshy and M. B. Turova-Polyak, Ber., 65, 1299 (1932): N. D. Zelinsky, Selected Works, Vol. II Acad. Sci. USSR Press, 1941, p. 263.

  7. W. F. Seyer, R. D. Walker, J. Am. Chem. Soc., 60, 2125 (1938).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of organic Chemistry of the USSR Academy of Sciences, USSR

    V. N. Setkina, D. N. Kursanov & A. L. Liberman

Authors
  1. V. N. Setkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. N. Kursanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. L. Liberman
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Setkina, V.N., Kursanov, D.N. & Liberman, A.L. Exchange of hydrogen atoms of saturated cyclic hydrocarbons with sulfuric acid. Russ Chem Bull 3, 89–94 (1954). https://doi.org/10.1007/BF01195428

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01195428

Keywords

Search

Navigation