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Reaction of m-nitro-p-toluenesulfonic acid N-nitroamide with small heterorings

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    n-Nitro-p-toluenesulfonic acid N-nitroamide adds to olefin oxides to give N-β-hydroxyalkylation products. The direction of the addition to monosubstituted oxides is such that the nitroamide anion adds to the most sterically available carbon atom.

  2. 2.

    m-Nitro-p-toluenesulfonic acid N-nitroamide reacts with unsubstituted ethylenimine to give the ethylenimine salt of the nitrosulfonamide.

  3. 3.

    m-Nitro-p-toluenesulfonic acid N-nitroamide reacts with an N-acylated ethylenimine or trimethylenimine with ring opening and the respective formation of N-β- or N-γ-amidoalkylation products.

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Literature cited

  1. P. A. Gembitskii, D. S. Zhuk, and V. A. Kargin, Ethylenimine Chemistry [in Russian], “Nauka” (1966).

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry of the Academy of Sciences of the USSR, Moscow

    A. A. Onishchenko, O. S. Reshetova, V. P. Gorelik, O. A. Luk'yanov & V. A. Tartakovskii

Authors
  1. A. A. Onishchenko
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  2. O. S. Reshetova
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  3. V. P. Gorelik
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  4. O. A. Luk'yanov
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  5. V. A. Tartakovskii
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1166–1168, May, 1976.

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Onishchenko, A.A., Reshetova, O.S., Gorelik, V.P. et al. Reaction of m-nitro-p-toluenesulfonic acid N-nitroamide with small heterorings. Russ Chem Bull 25, 1135–1137 (1976). https://doi.org/10.1007/BF00922010

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  • DOI: https://doi.org/10.1007/BF00922010

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