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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
Authors:V. Yu. Korotaev  V. Ya. Sosnovskikh  I. B. Kutyashev  M. I. Kodess
Affiliation:(1) A. M. Gorky Ural State University, 51 prosp. Lenina, 620083 Ekaterinburg, Russian Federation;(2) I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 ul. S. Kovalevskoi, 620219 Ekaterinburg, Russian Federation
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. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 309–321, February, 2006.
Keywords:2H-chromenes  chromanes  S-and N-nucleophiles  Michael reaction  diastereomers  conformers  NMR spectroscopy  X-ray diffraction analysis
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