Advertisement

Chemistry of Heterocyclic Compounds

, Volume 12, Issue 10, pp 1094–1097 | Cite as

Some chemical peoperties of 2-formyl-2,5-dialkoxy (alkylthio)-2, 3-dihydro-γ-pyrans

  • N. A. Keiko
  • L. G. Stepanova
  • I. D. Kalikhman
  • M. G. Voronkov
Article
  • 23 Downloads

Abstract

The conditions of heteropolar and radical thiylation of 2-formyl-2,5-diethoxy-2,3-dihydro-γ-pyrans were studied. Oxidation of the carbonyl group occurs along with the Cannizzaro reaction in the reaction of 2-formyl-2,5-diethoxy-2,3-dihydro-γ-pyran with silver oxide in alkaline media. Oxidation of 2-formyl-2,5-dibutylthio-2,3-dihydro-γ-pyran with silver oxide leads to stable 2,5-dibutylthio-2,3-dihydro-γ-pyran-2-carboxylic acid.

Keywords

Oxidation Organic Chemistry Carbonyl Carbonyl Group Alkaline Medium 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    N. A. Keiko, L. G. Stepanova, I. E. Kalikhman, G. I. Kirillova, and M. G. Voronkov, Khim. Geterotsikl. Soedin., No. 5, 602 (1975).Google Scholar
  2. 2.
    F. Kipnis, H. Soloway, and I. Ornfelt, J. Am. Chem. Soc.,73, 1783 (1951).Google Scholar
  3. 3.
    F. Kipnis and I. Ornfelt, J. Am. Chem. Soc.,73, 822 (1951).Google Scholar
  4. 4.
    G. F. Holland and L. Cohen, J. Am. Chem. Soc.,80, 3765 (1958).Google Scholar
  5. 5.
    W. E. Parham and D. M. Delaitsch, J. Am. Chem. Soc.,76, 4962 (1954).Google Scholar
  6. 6.
    M. F. Shostakovskii, E. N. Prilezhaeva, and É. S. Shapiro, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 357 (1953).Google Scholar
  7. 7.
    R. E. Bowman and D. W. Fordham, J. Chem. Soc., 3495 (1952).Google Scholar
  8. 8.
    C. W. Smith, Acrolein, John Wiley and Sons, Inc. (1962), p. 189.Google Scholar
  9. 9.
    T. Oca and V. Canami, J. Synthetic Org. Chem. Jpn.,25, 392 (1967).Google Scholar
  10. 10.
    I. I. Brezinski, D. G. Kubler, and A. E. Montagna, J. Org. Chem.,24, 1807 (1959).Google Scholar
  11. 11.
    R. Whetstone, J. Am. Chem. Soc.,73, 5280 (1951).Google Scholar
  12. 12.
    R. Whetstone, US Patent No. 2511890 (1950).Google Scholar

Copyright information

© Plenum Publishing Corporation 1977

Authors and Affiliations

  • N. A. Keiko
    • 1
  • L. G. Stepanova
    • 1
  • I. D. Kalikhman
    • 1
  • M. G. Voronkov
    • 1
  1. 1.Irkutsk Institute of Organic Chemistry, Siberian BranchAcademy of Sciences of the USSRUSSR

Personalised recommendations