Skip to main content
SpringerLink
Log in

Autooxidation of methylheterocycles under phase transfer catalysis conditions

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The autooxidation of methyl- and dimethyl-substituted N-, S-, and O-heterocyclic compound derivatives has been studied in 1,2-dimethoxyethane—t-BuOK in the presence of 18-crown-6. Mono- and dicarboxylic acid derivatives of pyrazine, pyridine, pyrimidine, and thiophene have been synthesized.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature Cited

  1. E. Demlow and Z. Demlow, Phase Transfer Catalysis [Russian translation], Mir, Moscow (1987).

    Google Scholar 

  2. G. A. Artamkina and I. P. Beletskaya, ZhVKhO, 31, 196 (1986).

    Google Scholar 

  3. R. Neumann and Y. Sasson, J. Org. Chem., 49, 1282 (1984).

    Google Scholar 

  4. G. A. Artamkina, A. A. Grinfel'd, and I. P. Beletskaya, Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2284 (1984).

    Google Scholar 

  5. G. A. Artamkina, A. A Grinfel'd, and I. P. Beletskaya, Tetrahedron Lett., 25, 4989 (1984).

    Google Scholar 

  6. I. G. Iovel', I. Ya. Yansone, Yu. Sh. Gol'dberg, and M. V. Shimanskaya, Khim. Geterotsikl. Soedin., No. 4, 532 (1990).

    Google Scholar 

  7. J. Joule and H. Smith, Principles of the Chemistry of Heterocyclic Compounds [Russian translation], Mir, Moscow (1975), p. 142.

    Google Scholar 

  8. I. P. Skibida, A. M. Sakharov, and O. N. Emanuel', Itogi Nauki i Tekhniki, Ser. Kinet. Katal., 15, 118 (1986).

    Google Scholar 

  9. E. M. Abele, Yu. Sh. Gol'dberg, Yu. Yu. Popelis, and M. V. Shimanskaya, Zh. Org. Khim., 26, 1784 (1990).

    Google Scholar 

  10. A. Gordon and R. Ford, The Chemist's Companion, Wiley-Interscience, New York (1972).

    Google Scholar 

  11. D. Pitre, S. Boveri, and E. B. Grabitz, Chem. Ber., 99, 364 (1966).

    Google Scholar 

  12. H. Gainer, J. Org. Chem., 24, 691 (1959).

    Google Scholar 

  13. G. Black, E. Depp, and B. B. Corson, J. Org. Chem., 14, 44 (1949).

    Google Scholar 

  14. T. V. Gortinskaya, K. M. Murav'eva, and M. N. Shchukina, Zh. Obshch. Khim., 25, 2313 (1955).

    Google Scholar 

  15. R. Lukes, V. Galik, and J. Jizba, Coll., 26, 2727 (1961).

    Google Scholar 

  16. H. Gilman, J. Am. Chem. Soc., 71, 1870 (1949).

    Google Scholar 

  17. A. A. Ponomarev, Synthesis and Reactions of Furan Derivatives [in Russian], Saratov Univ. Press (1960).

  18. W. Brügel, Z. Elektrochem., 66, 159 (1962).

    Google Scholar 

  19. D. J. Chadwick, J. Chambers, G. D. Meakins, and R. L. Snowden, J. Chem. Soc., Perkin Trans. 1, 201 (1973).

    Google Scholar 

  20. S. Gronowitz, J. Johnson, and A.-B. Hörnfeldt, Chem. Scr., 7, 211 (1975).

    Google Scholar 

  21. S. R. Heller and G. W. A. Miene, EPA/NJH Mass Spectra Data, Vol. 1, Washington (1978).

  22. Eight Peak Index of Mass Spectra, 2nd edn., Mass Spectrometry Data Centre, Aldermaston (1974).

  23. G. S. Marx and P. E. Spoerri, J. Org. Chem., 37, 111 (1972).

    Google Scholar 

  24. T. J. Batterham, NMR Spectra of Simple Heterocycles, Wiley-Interscience, New York (1975).

    Google Scholar 

  25. G. Levy and G. Nelson, Carbon-13 Nuclear Magnetic Resonance for Organic Chemists, Wiley-Interscience, New York (1972).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Synthesis, Latvian Academy of Sciences, Riga

    I. G. Iovel', Yu. Sh. Gol'dberg, A. P. Gaukhman, R. M. Zolotoyabko & M. V. Shimanskaya

Authors
  1. I. G. Iovel'
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu. Sh. Gol'dberg
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. P. Gaukhman
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. M. Zolotoyabko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. V. Shimanskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 959–962, July, 1991.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Iovel', I.G., Gol'dberg, Y.S., Gaukhman, A.P. et al. Autooxidation of methylheterocycles under phase transfer catalysis conditions. Chem Heterocycl Compd 27, 768–771 (1991). https://doi.org/10.1007/BF00476210

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00476210

Keywords

Search

Navigation