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Reactions of 3-nitro-2-trihalomethyl-2H-chromenes with S-and N-nucleophiles. Synthesis and stereochemistry of 2,3,4-trisubstituted chromanes

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Abstract

The reactions of 3-nitro-2-trifluoromethyl-and 3-nitro-2-trichloromethyl-2H-chromenes with thiols and aromatic amines proceed via the nucleophilic addition type to the activated double bond to form 2,3,4-trisubstituted chromanes in high yields. The stereoisomeric compositions and structures of the diastereomers were determined by 1H, 19F NMR and 2D NOESY spectroscopies and X-ray diffraction analysis.

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Authors and Affiliations

  1. A. M. Gorky Ural State University, 51 prosp. Lenina, 620083, Ekaterinburg, Russian Federation

    V. Yu. Korotaev, V. Ya. Sosnovskikh & I. B. Kutyashev

  2. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 ul. S. Kovalevskoi, 620219, Ekaterinburg, Russian Federation

    M. I. Kodess

Authors
  1. V. Yu. Korotaev
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  2. V. Ya. Sosnovskikh
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  3. I. B. Kutyashev
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  4. M. I. Kodess
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 309–321, February, 2006.

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Korotaev, V.Y., Sosnovskikh, V.Y., Kutyashev, I.B. et al. Reactions of 3-nitro-2-trihalomethyl-2H-chromenes with S-and N-nucleophiles. Synthesis and stereochemistry of 2,3,4-trisubstituted chromanes. Russ Chem Bull 55, 317–330 (2006). https://doi.org/10.1007/s11172-006-0255-6

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  • DOI: https://doi.org/10.1007/s11172-006-0255-6

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