Skip to main content
Log in

Kathodische Reduktion von α-Azidostyrolen

Cathodic reduction of α-azidostyroles. Electrolytic studies on vinylazides, I

Elektrolytische Untersuchungen an Vinylaziden. 1. Mitt.

  • Anorganische Und Physikalische Chemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

Cathodic reduction of non-terminal vinylazides on Hg cathodes in the presence of electrophiles gives reasonable yields of N-acylated enamines in an electrochemically totally irreversible reaction. In the presence of added H-donors rather high selectivity for formation of saturated amides is achieveable. The influence of reaction conditions on product distribution is discussed.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Hassner A., Acc. Chem. Res.4, 9 (1971).

    Google Scholar 

  2. L'abbé G., Angew. Chem.87, 831 (1975);

    Google Scholar 

  3. L'abbé G., Industrie Chim. BelgeT34, 519 (1969);

    Google Scholar 

  4. Boyer J. H., Krueger W. E., Modler R., J. Org. Chem.34, 1987 (1969);

    Google Scholar 

  5. Hassner A., Levy A. B., J. Amer. Chem. Soc.93, 5469 (1971);

    Google Scholar 

  6. Patai S., The Chemistry of the Azido Group. Interscience. 1974.

  7. Lund H., Österr. Chem. Ztg.68, 43 (1967).

    Google Scholar 

  8. Malyugina N. I., Vertyulina L. N., Koryttsev N. K., Oleinik A. V., Zh. Obsch. Khim.44, 478 (1974).

    Google Scholar 

  9. Knittel D., VII. Scandinavian Meeting on Organic Electrochemistry, Sandbjerg, 1978.

  10. Lund H., Simonet J., C.R. Acad. Sci., Ser. C277, 1387 (1973);Lund H., Degrand Ch., Tetrahedron Lett.1977, 3593;Christensen L., Iversen P. E., Acta Chem. Scand.B 33, 352 (1979);Shono T., Nishiguchi I. H., Ohmizu H., J. Amer. Chem. Soc.99, 7396 (1977).

    Google Scholar 

  11. Mann C. K.,Barnes K. K., Electrochemical Reactions in Nonaqueous Solutions. Marcel Dekker. 1970.

  12. Cook A. G., Enamines. Marcel Dekker. 1969.

  13. Suen Y. H., Kagan H. B., Bull. Soc. Chim. Fr.32, 1460 (1965).

    Google Scholar 

  14. Knittel D., Monatsh. Chem.113, 37 (1982).

    Google Scholar 

  15. Smolinsky G., J. Amer. Chem. Soc.83, 4483 (1961).

    Google Scholar 

  16. Lalonde R. T., Davies C. B., J. Org. Chem.35, 771 (1970).

    Google Scholar 

  17. Knittel D., Henning A., Monatsh. Chem.115, 391 (1984).

    Google Scholar 

  18. Stocker J. H., Kern D. H., Jenevein R. M., J. Org. Chem.33, 412 (1968).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Knittel, D. Kathodische Reduktion von α-Azidostyrolen. Monatsh Chem 115, 523–531 (1984). https://doi.org/10.1007/BF00799159

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00799159

Keywords

Navigation