Monatshefte für Chemie / Chemical Monthly

, Volume 116, Issue 8–9, pp 1041–1049 | Cite as

3-Oxo-2-tosyloxy-1-alkenylphosphonsäuredialkylester als Synthone zum Aufbau von Hetarylphosphonsäuredialkylestern

  • Gottfried Penz
  • Erich Zbiral
Organische Chemie And Biochemie

Dialkyl 3-oxo-2-tosyloxy-1-alkenylphosphonates—Synthones for the preparation of dialkyl hetarylphosphonates


The title compounds4 react with amidines to give pyrimidinylphosphonates6 and pyrimidinonderivatives8, respectively. Otherwise the pyridinylphosphonate7 and the 2-pyridonderivative9 are formed only in small amounts by treating4 with 3-amino-2-butenoate. With hydrazine compound4 affords pyrazolylphosphonates10 and the pyrazolonylderivative11. 4-Acyl-1,2,3-triazolylphosphonates12 can easily be prepared by reaction of4 with sodium azide.


Dialkyl 3-oxo-2-tosyloxy-1-alkenylphosphonates, reaction with bidentate (ambient) nucleophiles Hetarylphosphonates Reactivity, comparison between 3-oxo-1-alkenylphosphonium salts and 3-oxo-1-alkenylphosphonates 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1 a).
    Hildebrand R. L., Curley-Joseph J., Lubansky H. J., Henderson T. O., Top. Phosphorus Chem.11, 297 (1983).Google Scholar
  2. 1 b).
    Hemmi K., Takeno H., Hasimoto M., Kamiya T., Chem. Pharm. Bull.30, 111 (1982).Google Scholar
  3. 1 c).
    Vasella A., Voeffray R., Helv. Chim. Acta65, 1953 (1982).Google Scholar
  4. 2.
    Hammerschmidt F.,Zbiral E., Liebigs Ann. Chem.1979, 492.Google Scholar
  5. 3 a).
    Penz G., Zbiral E., Monatsh. Chem.113, 1169 (1982).Google Scholar
  6. 3 b).
    Öhler E., Zbiral E., El-Badawi M., Tetrahedron Lett.24, 5599 (1983).Google Scholar
  7. 3 c).
    Öhler E., Zbiral E., Monatsh. Chem.115, 493 (1984).Google Scholar
  8. 3 d).
    Öhler E., Zbiral E., Monatsh. Chem.115, 629 (1984).Google Scholar
  9. 3 e).
    Öhler E., El-Badawi M., Zbiral E., Chem. Ber.117, 3034 (1984).Google Scholar
  10. 4.
    Zbiral E., in: Organophosphorus Reagents in Organic Synthesis (Cadogan J. I. G., Hrsg.), S. 256–268. London: Academic Press.1979.Google Scholar
  11. 5.
    Dodson R. M., Seyler J. K., J. Org. Chem.16, 461 (1951).Google Scholar
  12. 6.
    Penz G.,Zbiral E., Chem. Ber., im Druck.Google Scholar
  13. 7.
    Maruyama T., Taira Z., Horikawa M., Sato Y., Honjo M., Tetrahedron Lett.24, 2571 (1983).Google Scholar
  14. 8.
    Aoyama T., Inoue S., Shiori T., Tetrahedron Lett.25, 433 (1984).Google Scholar

Copyright information

© Springer-Verlag 1985

Authors and Affiliations

  • Gottfried Penz
    • 1
  • Erich Zbiral
    • 1
  1. 1.Institut für Organische ChemieUniversität WienWienÖsterreich

Personalised recommendations