Skip to main content

Oxime Derivatives. VIII. Polarographic Reduction of O- and N-Substituted Oximes

  • Chapter
Topics In Organic Polarography
  • 184 Accesses

Abstract

Reduction of nine N-substituted oximes (nitrones) IIX and of seven O-substituted oximes XIXVII at the dropping mercury electrode was investigated. Aromatic N-substituted derivatives are reduced in acid as well as in alkaline media in one four-electron wave to the secondary amine; the reduction proceeds through the corresponding Schiff base. The behaviour of aromatic O-alkyl derivatives in acid media is similar to that of corresponding N-alkyl derivatives whereas in alkaline solutions O-alkyl derivatives do not show a reduction wave. Aliphatic N-derivatives are reduced in acid media only and aliphatic O-derivatives are principally polarographically inactive. In all instances, both isomeric derivatives can be safely distinguished by polarography.

Part VII.: This Journal 28, 3150 (1963).

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

Access this chapter

eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Exner O.: This Journal 20, 202 (1955); Chem. listy 48, 1543 (1954).

    CAS  Google Scholar 

  2. Emmons W. D.: J. Am. Chem. Soc. 79, 5739 (1957).

    Article  CAS  Google Scholar 

  3. Horner L., Jürgens E.: Chem. Ber. 90, 2184 (1957).

    Article  CAS  Google Scholar 

  4. Cope A. C., Haven A. C.: J. Am. Chem. Soc. 72, 4896 (1950).

    Article  CAS  Google Scholar 

  5. Alessandri L.: Gazz. Chim. Ital. 51, I., 75 (1921).

    Google Scholar 

  6. Martynoff M.: Ann. Chim. (Paris) [11] 7, 424 (1937).

    CAS  Google Scholar 

  7. Semper L., Lichtenstadt L.: Ber. 51, 928 (1918).

    CAS  Google Scholar 

  8. Brady O. L., Dunn F. P., Goldstein R. F.: J. Chem. Soc. 1926, 2386.

    Google Scholar 

  9. Beckmann E.: Ann. 367, 211 (1909).

    Google Scholar 

  10. Krimm H.: Chem. Ber. 91, 1057 (1958).

    Article  CAS  Google Scholar 

  11. Reiser A., Jehlicka V., Dvorak K.: This Journal 16, 13 (1951).

    CAS  Google Scholar 

  12. Vavon G., Crajcinovic: Compt. Rend. 187, 420 (1928).

    CAS  Google Scholar 

  13. Frumkin A. N.: Trans. Faraday Soc. 55, 156 (1959); where further references are given.

    Article  CAS  Google Scholar 

  14. Tondeur J. J., Dombret A., Gierst L.: J. Electroanal. Chem. 3, 225 (1962).

    Article  CAS  Google Scholar 

  15. Zuman P.: Unpublished results.

    Google Scholar 

  16. Koutecky J.: This Journal 18, 597 (1953); Chem. listy 47, 323 (1953).

    CAS  Google Scholar 

  17. Majranovskij S. G., Lisceta L. I.: This Journal 25, 3025 (1960).

    Google Scholar 

  18. Holleck L., Kastening B.: Z. Elektrochem. 60, 127 (1956).

    CAS  Google Scholar 

  19. Kastening B., Holleck L., Melkonian G. A.: Z. Elektrochem. 60, 130 (1956).

    CAS  Google Scholar 

  20. Taft R. W., jr.: Separation of Polar, Steric, and Resonance Effects in Reactivity in the book: Steric Effects in Organic Chemistry (M. S. Newman, Ed.). Wiley, New York 1956.

    Google Scholar 

  21. Zuman P.: This Journal 25, 3025 (1960).

    Google Scholar 

  22. Vodräzka Z.: Chem. listy 46, 208 (1952).

    Google Scholar 

  23. Jones L. W., Sneed M. C.: J. Am. Chem. Soc. 39, 674 (1917).

    Article  CAS  Google Scholar 

  24. Souchay P., Ser S.: J. Chim. Phys. 49, C 172 (1952).

    Google Scholar 

  25. Lund H.: Acta Chem. Scand. 13, 249 (1959).

    Article  CAS  Google Scholar 

  26. Earl J. C.: Ree. Trav. Chim. 75, 346 (1956).

    Article  CAS  Google Scholar 

  27. Cusmano G.: Gazz. Chim. Ital. 51, II., 306 (1921).

    Google Scholar 

  28. Brewster J. H.: J. Am. Chem. Soc. 76, 6361 (1954).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1970 Plenum Publishing Company Ltd.

About this chapter

Cite this chapter

Zuman, P., Exner, O. (1970). Oxime Derivatives. VIII. Polarographic Reduction of O- and N-Substituted Oximes. In: Zuman, P. (eds) Topics In Organic Polarography. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-1812-5_34

Download citation

  • DOI: https://doi.org/10.1007/978-1-4684-1812-5_34

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-1814-9

  • Online ISBN: 978-1-4684-1812-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics