Chemistry of Natural Compounds

, Volume 10, Issue 3, pp 364–370 | Cite as

Claisen rearrangement of alkoxyquinol-2-ones in mass spectrometry

  • Ya. V. Rashkes
  • I. A. Bessonova
  • S. Yu. Yunusov
Article
  • 18 Downloads

Conclusions

Claisen rearrangements of bucharaine acetonide and its N-methyl derivative take place in the inlet system of a mass spectrometer at 90–110°C. At 180°C, an anomalous rearrangement is the main process, accompanied by the formation of dihydrofuranoquinolinone derivatives.

A similar process is observed in the γ, γ-dimethylallyl ethers of some hydroxyqinol-2-ones.

Keywords

CD3OD Acetonide Caustic Soda Inlet System Anhydrous Potassium Carbonate 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    Ya. V. Rashkes, Z. Sh. Faizutdinova, I. A. Bessonova, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 577 (1970).Google Scholar
  2. 2.
    E. N. Marvell, D. R. Anderson, and J. Ong., J. Org. Chem.,27, 1109 (1962); A. Jefferson and F. Scheinmann, Quart. Rev.,22, 391 (1968).CrossRefGoogle Scholar
  3. 3.
    Ya. V. Rashkes, I. A. Bessonova, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 336 (1972).Google Scholar
  4. 4.
    I. A. Bessonova, Ya. V. Rashkes, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 358 (1974).Google Scholar
  5. 5.
    R. Woodward and R. Hoffman, The Conservation of Orbital Symmetry, Academic Press, New York (1970); G. B. Gill, Quart. Rev., 22, 338 (1968).Google Scholar
  6. 6.
    B. D. Paul and P. K. Bose, J. Indian Chem. Soc.,45, 552 (1968); Indian J. Chem.,7, 678 (1969).Google Scholar
  7. 7.
    N. S. Vul'fson, V. I. Zaretskii, and V. G. Zaikin, Dokl. Akad. Nauk. SSSR,155, 1104 (1964).Google Scholar
  8. 8.
    V. N. Zvolinskii, M. E. Perel'son, and Yu. N. Sheinker, Teoret. Éksperim., Khim.,6, 250 (1970).Google Scholar

Copyright information

© Plenum Publishing Corporation 1975

Authors and Affiliations

  • Ya. V. Rashkes
  • I. A. Bessonova
  • S. Yu. Yunusov

There are no affiliations available

Personalised recommendations