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First example of regioselective nucleophilic 1,6-addition of trimethyl(trifluoromethyl)silane to 4H-chromene derivatives

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Abstract

Condensation of 2-trifluoromethylchromone with diethyl malonate, ethyl cyanoacetate, and Meldrum’s acid gave the corresponding methylidene derivatives of 2-trifluoromethyl-4H-chromene. Nucleophilic 1,6-addition of an excess of Me3SiCF3 in the presence of Me4NF to those obtained from the former two compounds afforded 4-substituted 2,2-bis(trifluoromethyl)-2H-chromenes.

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Authors and Affiliations

  1. A. M. Gor’kii Ural State University, 51 prosp. Lenina, 620083, Ekaterinburg, Russian Federation

    V. Ya. Sosnovskikh, B. I. Usachev & M. N. Permyakov

  2. Institute of Inorganic and Physical Chemistry, University of Bremen, Leobener Strasse, 28334, Bremen, Germany

    D. V. Sevenard & G.-V. Röschenthaler

Authors
  1. V. Ya. Sosnovskikh
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  2. B. I. Usachev
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  3. M. N. Permyakov
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  4. D. V. Sevenard
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  5. G.-V. Röschenthaler
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1628–1630, September, 2006.

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Sosnovskikh, V.Y., Usachev, B.I., Permyakov, M.N. et al. First example of regioselective nucleophilic 1,6-addition of trimethyl(trifluoromethyl)silane to 4H-chromene derivatives. Russ Chem Bull 55, 1687–1689 (2006). https://doi.org/10.1007/s11172-006-0475-9

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  • DOI: https://doi.org/10.1007/s11172-006-0475-9

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