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Synthesis and investigation of aziridino dioximes

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reactions of chloroglyoximes with substituted aziridines were investigated. In the case of donor substituents in the aziridine the reaction takes place with the formation of anti-aziridino dioximes, while the formation of furoxanoglyoximes is also observed when electron-acceptor substituents are present. Aziridinofuroxans were obtained by oxidation of the aziridino dioximes. The barrier to inversion of the nitrogen atom in the aziridinofuroxans is 12.0 kcal/mole. The expansion of the aziridine ring of the aziridino dioximes, which leads to the formation of 1,2,4-oxadiazines, was investigated.

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Literature cited

  1. C. Grundmann and P. Grünanger, The Nitrile Oxides, Springer Verlag, Berlin (1971).

    Google Scholar 

  2. P. Walstra, W. Trompen, and J. Hackmann, Recl. Trav. Chim., 87, 452 (1968).

    Google Scholar 

  3. R. Gagneux and R. Meier, Helv. Chim. Acta, 53, 219 (1970).

    Google Scholar 

  4. F. A. Anet and J. Yavari, Org. Magn. Reson., 8, 158 (1976).

    Google Scholar 

  5. L. Stefaniak, M. Witanovski, and G. A. Webb, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 26, 281 (1978).

    Google Scholar 

  6. C. W. Bird, Tetrahedron Lett., No. 9, 1703 (1976).

    Google Scholar 

  7. P. Rajagopalan and C. N. Talatu, J. Am. Chem. Soc., 88, 50 (1966).

    Google Scholar 

  8. V. M. Peshkova, V. M. Savostina, and E. K. Ivanova, Oximes [in Russian], Nauka, Moscow (1977).

    Google Scholar 

  9. É. É. Liepin'sh, A. V. Eremeev, D. A. Tikhomirov, and R. S. Él'kinson, Khim. Geterotsikl. Soedin., No. 3, 338 (1978).

    Google Scholar 

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Authors and Affiliations

  1. Institute of Organic Synthesis, Academy of Sciences of the Latvian SSR, 226006, Riga

    A. V. Eremeev, I. P. Piskunova, V. G. Andrianov & É. É. Liepin'sh

Authors
  1. A. V. Eremeev
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  2. I. P. Piskunova
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  3. V. G. Andrianov
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  4. É. É. Liepin'sh
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 488–494, April, 1982.

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Eremeev, A.V., Piskunova, I.P., Andrianov, V.G. et al. Synthesis and investigation of aziridino dioximes. Chem Heterocycl Compd 18, 369–374 (1982). https://doi.org/10.1007/BF00503555

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  • DOI: https://doi.org/10.1007/BF00503555

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