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.
Similar content being viewed by others
Literature cited
P. A. Sharbatyan, A. T. Lebedev, A. M. Sipyagin, V. G. Kartsev, and V. S. Petrosyan, Khim. Ceterotsikl. Soedin., No. 3, 334 (1982).
V. C. Kartsev and A. M. Sipyagin, Zh. Org. Khim.,15, 2603 (1979).
C. W. Thomas and L. L. Leverson, Org. Mass Spectrom.,13, 39 (1978).
K.-P. Zeller, H. Meier, and E. Muller, Tetrahedron,28, 5831 (1972).
K.-P. Zeller and P. Klaus, Org. Mass Spectrom.,10, 317 (1975).
K. Undheim and O. Thorstael, Org. Mass Spectrom.,5, 73 (1971).
R. A. Khmel'nitskii and Yu. A. Efremov, Usp. Khim.,46, 83 (1977).
H.-W. Leung and A. G. Harrison, J. Am. Chem. Soc.,101, 3147 (1979).
H.-W. Leung and A. G. Harrison, J. Am. Chem. Soc.,102, 1623 (1980).
Author information
Authors and Affiliations
Additional information
See [1] for Communication 1.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 919–925, July, 1982.
Rights 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
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00568945