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Mass-spectrometric study of the cyclization reactions of diazoketones. 8. 1-Diazo-3,4-epoxy-4-arylbutan-2-ones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

An analysis of the mass spectra of 1-diazo-3,4-epoxy-4-arylbutanones has shown that the molecular ions of these compounds lose a molecule of nitrogen and that the [M — N2]+ ions formed cyclize to form hydroxyfuran structures, whose further fragmentation determines the whole picture of the dissociative ionization of the compounds investigated under electron impact. The majority of the [M — N2]+ ions have the form of the cyclic intermediate formed in the first step of the cyclization process. It cannot, however, be ruled out that a certain portion of the [M — N2]+ ions are stabilized as a result of a Wolff rearrangement and do not cyclize at all.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, 117234, Moscow

    A. T. Lebedev, P. A. Sharbatyan, A. G. Kazaryan, T. P. Pokidova, V. G. Kartsev & V. S. Petrosyan

Authors
  1. A. T. Lebedev
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  2. P. A. Sharbatyan
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  3. A. G. Kazaryan
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  4. T. P. Pokidova
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  5. V. G. Kartsev
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  6. V. S. Petrosyan
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Additional information

For report 7 see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 17–22, January, 1986.

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Lebedev, A.T., Sharbatyan, P.A., Kazaryan, A.G. et al. Mass-spectrometric study of the cyclization reactions of diazoketones. 8. 1-Diazo-3,4-epoxy-4-arylbutan-2-ones. Chem Heterocycl Compd 22, 13–18 (1986). https://doi.org/10.1007/BF00515415

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  • DOI: https://doi.org/10.1007/BF00515415

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