Skip to main content
SpringerLink
Log in

Beiträge zur Stereochemie der Additionsreaktionen an 3,4,5,6-Tetrahydropyridin-1-oxide. 2. Mitt.

Die Cyclodimerisierung alkylsubstituierter 3,4,5,6-Tetrahydropyridin-1-oxide als Beispiel für die Stereochemie einer [3+3]-Addition

Contributions to the stereochemistry of additionreactions to 3,4,5,6-tetrahydropyridine-1-oxide. 2. comm.: Cyclodimerization of alkylsubstituted 3,4,5,6-tetrahydropyridine-1-oxides as an example of the stereochemistry of a [3+3]-addition

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

4-tert-Butyl-3,4,5,6-tetrahydropyridine-1-oxide (1) and 6-butyl-3,4,5,6-tetrahydropyridine-1-oxide (2) were prepared and isolated in their monomeric forms. In many aprotic solvents these compounds are converted into their dimers. The main product in both cases is the addition product of identical enantiomers. In the case of compound1 a very small amount of an addition product of the optical antipodes is also formed, which is the thermodynamically most stable isomer. In contrast, compound2 yielded an addition product of the optical antipodes in larger amounts, with a thermodynamically less favourable structure. These dimerizations are solvent dependent, reversible and sensitive to steric hindrance.

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

Literatur

  1. 1. Mitt.:Gössinger E., Mh. Chem.112, 1017 (1981).

    Google Scholar 

  2. Gössinger E., Imhof R., Wehrli H., Helv. Chim. Acta58, 96 (1975);

    Google Scholar 

  3. Gössinger E., Mh. Chem.111, 143 (1980);

    Google Scholar 

  4. Gössinger E., Tetrahedron Lett.1980, 2229;

  5. Gössinger E., Mh. Chem.111, 783 (1980);

    Google Scholar 

  6. Gössinger E., Witkop B., Mh. Chem.111, 803 (1980).

    Google Scholar 

  7. Huisgen R., Angew. Chem.75, 604 (1963).

    Google Scholar 

  8. Wiley P. F., in: The Chemistry of Heterocyclic Compounds, Bd. 33 (Weissberger A.,Taylor E. C., Hrsg.), S. 1190 ff. und S. 1274 ff. Wiley Interscience. 1978. Siehe auch die dort zitierte Literatur.

  9. Ahlbrecht H.,Fröhlich J.,Habermalz U.,Kröhnke F., Tetrahedron Lett.1967, 3649;Petrovanu M.,Stefanescu E.,Druta I., Rev. Roum. Chim.16, 1107 (1971);Petrovanu M.,Saucine A.,Gabe I.,Zugravescu I., Rev. Roum. Chim.14, 1153 (1969);Caprosu M.,Petrovanu M.,Druta I.,Zugravescu I., Bull. Soc. Chim. France1971, 1834;Huisgen R.,Grashey R.,Krischke R., Tetrahedron Lett.1962, 387;Müller G.,Duchardt K. H.,Kröhnke F., Chem. Ber.110, 3224 (1977);Zugravescu I.,Georgescu F. C.,Chiralev F.,Filip P.,Georgescu E. I., Rev. Chim. (Bucuresti)31, 11 (1980).

  10. Huisgen R.,Grashey R.,Krischke R., Tetrahedron Lett.1962, 387.

  11. Guingant A.,Renault J., Bull. Soc. Chim. France1976, 291.

  12. Gotthardt H.,Weisshuhn C. M.,Huss O. M.,Brauer D. J., Tetrahedron Lett.1978, 671.

  13. Winterfeldt E., Krohn W., Stracke H., Chem. Ber.102, 2346 (1969);Kliegel W., Tetrahedron Lett.1969, 2627;Reamer R. A., Sletzinger M., Shinkai I., Tetrahedron Lett.1980, 3447;Baker A. D., Baldwin J. E., Kelly D. P., DeBernards J., J. Chem. Soc., Chem. Com.1969, 344.

    Google Scholar 

  14. Thesing J., Mayer H., Chem. Ber.89, 2159 (1956);

    Google Scholar 

  15. Thesing J., Mayer H., Liebigs Ann. Chem.609, 46 (1957);

    Google Scholar 

  16. Eikelmann G., Heimberger W., Nonnenmacher G., Weigert W. M., Liebigs Ann. Chem.759, 183 (1972);

    Google Scholar 

  17. Colonna M., DeMartino U., Gazetta93, 1183 (1963).

    Google Scholar 

  18. Katritzky A. R.,Patel R.,Saba S.,Harlow R. L.,Simonsen St. H., J. Chem. Soc. Perkin II1978, 818.

  19. Hamer J., Macaluso A., Chem. Rev.64, 473 (1964);

    Google Scholar 

  20. Delpierre G. R., Lamchen M., Quart. Rev.19, 337 (1965);

    Google Scholar 

  21. Rundel W., in: Houben-Weyl, Methoden der Org. Chemie, Bd. 10/4, Die Nitrone, S. 420 ff. Stuttgart: G. Thieme.

  22. Belg. P. 615736 (1962), Erf.Smith H. R., C.A. 59, 455 (1963).

    Google Scholar 

  23. Lit. cit. 12c.Rundel W., in: Houben-Weyl, Methoden der Org. Chemie, Bd. 10/4, Die Nitrone, S. 420 ff. Stuttgart: G. Thieme.

  24. Rolfe R. E.,Sales K. D.,Utley J. H. P., J. Chem. Soc. Perkin II1973, 1171.

  25. Lemieux R. U., Stevens J. D., Canad. J. Chem.44, 249 (1966).

    Google Scholar 

  26. Eliel E. L., Kandasamy D., Yeu Chen-yu, Hargrave K. D., J. Amer. Chem. Soc.102, 3698 (1980).

    Google Scholar 

  27. Anet F. A. L.,Yavari I., Tetrahedron Lett.1977, 3207.

  28. Johnson F., Chem. Rev.68, 375 (1968).

    Google Scholar 

  29. Barna J. C. J.,Robinson M. J. T., Tetrahedron Lett.1979, 1459;

  30. Bock K.,Pedersen C., J. Chem. Soc. Perkin II1974, 293.

  31. In jüngster Zeit wurde über die Cyclodimerisierung eines Nitrons im fünfgliedrigen Ring berichtet:Epstein S. P.,Simonova T. G.,Putsykin Y. G.,Baskakov Y. A., Khim. Geterotsikl. Soedin.1980, 1670.

  32. Gössinger E., Mh. Chem. im Druck.

Download references

Author information

Authors and Affiliations

  1. Institut für Organische Chemie, Universität Wien, A-1090, Wien, Österreich

    Edda Gössinger

Authors
  1. Edda Gössinger
    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

Gössinger, E. Beiträge zur Stereochemie der Additionsreaktionen an 3,4,5,6-Tetrahydropyridin-1-oxide. 2. Mitt.. Monatsh Chem 113, 339–354 (1982). https://doi.org/10.1007/BF00799561

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00799561

Keywords

Search

Navigation