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2-Polyfluoroalkylchromones. 10. Synthesis of regioisomeric 3-(2-hydroxyaryl)-5-polyfluoroalkyl- and 5-(2-hydroxyaryl)-3-polyfluoroalkylisoxazoles and determination of their structures by 1H, 19F, and 13C NMR spectroscopy

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Abstract

The reactions of 2-hydroxy-2-polyfluoroalkylchroman-4-ones with hydroxylamine yield, through Δ2-isoxazolines as intermediate products, 3-(2-hydroxyaryl)-5-polyfluoroalkylisoxazoles. Analogous reactions with 2-polyfluoroalkylchromones afford β-diketone monooximes, which in an acidic medium undergo cyclodehydration into 5-(2-hydroxyaryl)-3-polyfluoroalkylisoxazoles. The structures of regioisomeric 3- and 5-polyfluoroalkylisoxazoles were determined using 1H, 19F, and 13C NMR spectroscopy.

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

    V. Ya. Sosnovskikh, A. Yu. Sizov & B. I. Usachev

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  1. V. Ya. Sosnovskikh
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  2. A. Yu. Sizov
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Sosnovskikh, V.Y., Sizov, A.Y. & Usachev, B.I. 2-Polyfluoroalkylchromones. 10. Synthesis of regioisomeric 3-(2-hydroxyaryl)-5-polyfluoroalkyl- and 5-(2-hydroxyaryl)-3-polyfluoroalkylisoxazoles and determination of their structures by 1H, 19F, and 13C NMR spectroscopy. Russian Chemical Bulletin 51, 1270–1279 (2002). https://doi.org/10.1023/A:1020908831426

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