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Reaction of (E)-1,1,1-trichloro-3-nitrobut-2-ene with amines: diastereoselective synthesis of N-substituted α-trichloromethyl-β-nitroamines

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Abstract

The addition of primary and secondary amines to (E)-1,1,1-trichloro-3-nitrobut-2-ene proceeded diastereoselectively and led to a number of new N-substituted α-trichloromethyl-β-nitroamines, whose stereochemistry was confirmed by X-ray crystallography and NMR spectroscopy.

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Authors and Affiliations

  1. B. N. El’tsin Ural Federal University, 51 prosp. Lenina, 620083, Ekaterinburg, Russian Federation

    A. Yu. Barkov, V. Yu. Korotaev & V. Ya. Sosnovskikh

  2. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 ul. S. Kovalevskoi, 620041, Ekaterinburg, Russian Federation

    P. A. Slepukhin & M. I. Kodess

Authors
  1. A. Yu. Barkov
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  2. V. Yu. Korotaev
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  3. P. A. Slepukhin
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  4. M. I. Kodess
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  5. V. Ya. Sosnovskikh
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Corresponding author

Correspondence to V. Yu. Korotaev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1548–1553, August, 2012.

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Barkov, A.Y., Korotaev, V.Y., Slepukhin, P.A. et al. Reaction of (E)-1,1,1-trichloro-3-nitrobut-2-ene with amines: diastereoselective synthesis of N-substituted α-trichloromethyl-β-nitroamines. Russ Chem Bull 61, 1564–1569 (2012). https://doi.org/10.1007/s11172-012-0207-2

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  • DOI: https://doi.org/10.1007/s11172-012-0207-2

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