Skip to main content
SpringerLink
Log in

Saturated nitrogen-containing heterocycles. 13. Perhydroacridines. Synthesis and stereochemistry

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The configurations of the perhydroacridines formed in the catalytic hydroamination of threo-methylenedicyclohexanone and the product of its cyclization — 2-hydroxy-2,3-tetramethylenebicyclo[3.3.1]nonan-9-one — were established by means of the 13C NMR spectra and alternative synthesis. It is shown that isomers with cis-anti-cis and cis-syn-cis configurations are formed as a result of the reactions. The results of x-ray diffraction analysis are presented for cis-syn-cis-N-(2-hydroxyethy1)perhydroacridine.

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. A. P. Kriven'ko, T. G. Nikolaeva, A. A. Espenbetov, N. T. Komyagin, N. N. Sorokin, Yu. T. Struchkov, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 1, 71 (1985).

    Google Scholar 

  2. V. G. Kharchenko, A. P. Kriven'ko, O. V. Fedotova, and T. G. Nikolaeva, Khim. Geterotsikl. Soedin., No. 7, 944 (1982).

    Google Scholar 

  3. T. G. Nikolaeva, P. V. Reshetov, A. P. Kriven'ko, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 10, 1370 (1983).

    Google Scholar 

  4. N. Barbulescu, F. Potmischil, and D. Römer, Rev. Rom. Chim., 15, 1601 (1970).

    Google Scholar 

  5. V. I. Vysotskii, Khim. Geterotsikl. Soedin., No. 9, 1236 (1970).

    Google Scholar 

  6. E. L. Eliel and F. W. Vierhapper, J. Org. Chem., 41, 199 (1976).

    Google Scholar 

  7. F. W. Vierhapper and E. L. Eliel, J. Org. Chem., 42, 51 (1977).

    Google Scholar 

  8. P. Vanhee, F. D. Pessemiev, M. Anteunis, and D. Tavernier, Rec. Trav. Chim., 98, 294 (1979).

    Google Scholar 

  9. C. Altona and M. Sundaralingam, Tetrahedron, 26, 925 (1970).

    Google Scholar 

  10. K. A. Nirmala and D. S. S. Gowda, Acta Cryst., B28, 839 (1982).

    Google Scholar 

  11. M. Cygler, Acta Cryst., B37, 1771 (1981).

    Google Scholar 

  12. L. E. Sutton (editor), Tables of Interatomic Distances and Configurations in Molecules and Ions, London (1968).

  13. P. G. Gerr, A. I. Yanovskii, and Yu. T. Struchkov, Kristallografiya, No. 5, 1029 (1983).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. G. Chernyshevskii Saratov State University, 410601, Saratov

    A. P. Kriven'ko, T. G. Nikolaeva, L. M. Yudovich, N. T. Komyagin, A. I. Yanovskii, Yu. T. Struchkov & V. G. Kharchenko

Authors
  1. A. P. Kriven'ko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. G. Nikolaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. M. Yudovich
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. T. Komyagin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. I. Yanovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yu. T. Struchkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. V. G. Kharchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

See [1] for Communication 12.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1645–1650, December, 1987.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kriven'ko, A.P., Nikolaeva, T.G., Yudovich, L.M. et al. Saturated nitrogen-containing heterocycles. 13. Perhydroacridines. Synthesis and stereochemistry. Chem Heterocycl Compd 23, 1324–1329 (1987). https://doi.org/10.1007/BF00472257

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00472257

Keywords

Search

Navigation