Skip to main content
Log in

Mass-spectrometric study of the cyclization of diazo ketones. 2. Cyclization of 1-diazo-4-sulfonylaminobutan-2-ones to N-sulfonylpyrrolidin-3-ones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A comparison of the mass spectra of 1-diazo-4-sulfonylamino-butan-2-ones and N-sulfonylpyrrolidin-3-ones makes it possible to conclude that under the conditions of electron impact and chemical ionization the molecular ions of the investigated diazo ketones lose a molecule of nitrogen and undergo partial cyclization to the corresponding pyrrolidinones without undergoing the Wolff rearrangement.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. P. A. Sharbatyan, A. T. Lebedev, A. M. Sipyagin, V. G. Kartsev, and V. S. Petrosyan, Khim. Ceterotsikl. Soedin., No. 3, 334 (1982).

    Google Scholar 

  2. V. C. Kartsev and A. M. Sipyagin, Zh. Org. Khim.,15, 2603 (1979).

    Google Scholar 

  3. C. W. Thomas and L. L. Leverson, Org. Mass Spectrom.,13, 39 (1978).

    Google Scholar 

  4. K.-P. Zeller, H. Meier, and E. Muller, Tetrahedron,28, 5831 (1972).

    Google Scholar 

  5. K.-P. Zeller and P. Klaus, Org. Mass Spectrom.,10, 317 (1975).

    Google Scholar 

  6. K. Undheim and O. Thorstael, Org. Mass Spectrom.,5, 73 (1971).

    Google Scholar 

  7. R. A. Khmel'nitskii and Yu. A. Efremov, Usp. Khim.,46, 83 (1977).

    Google Scholar 

  8. H.-W. Leung and A. G. Harrison, J. Am. Chem. Soc.,101, 3147 (1979).

    Google Scholar 

  9. H.-W. Leung and A. G. Harrison, J. Am. Chem. Soc.,102, 1623 (1980).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

See [1] for Communication 1.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 919–925, July, 1982.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lebedev, A.T., Sharbatyan, P.A., Sipyagin, A.M. et al. Mass-spectrometric study of the cyclization of diazo ketones. 2. Cyclization of 1-diazo-4-sulfonylaminobutan-2-ones to N-sulfonylpyrrolidin-3-ones. Chem Heterocycl Compd 18, 697–703 (1982). https://doi.org/10.1007/BF00568945

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00568945

Keywords

Navigation