Publication: Efficient synthesis of fluoroalkylated 1,4,2-oxathiazoles via regioselective [3 + 2]-cycloaddition of fluorinated nitrile oxides with thioketones
Efficient synthesis of fluoroalkylated 1,4,2-oxathiazoles via regioselective [3 + 2]-cycloaddition of fluorinated nitrile oxides with thioketones
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Mlostoń, G., Kowalski, M. K., Obijalska, E., & Heimgartner, H. (2017). Efficient synthesis of fluoroalkylated 1,4,2-oxathiazoles via regioselective [3 + 2]-cycloaddition of fluorinated nitrile oxides with thioketones. Journal of Fluorine Chemistry, 199, 92–96. https://doi.org/10.1016/j.jfluchem.2017.04.011
Abstract
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Abstract
Fluorinated acetonitrile oxides, generated from the corresponding hydroximoyl bromides in the presence of aryl, hetaryl, ferrocenyl, and cycloaliphatic thioketones, undergo efficient [3 + 2]-cycloadditions to give 3- fluoroalkylated 1,4,2-oxathiazoles in good to excellent yields. The reactions proceed regioselectively with no competitive formation of furoxans as dimers of the intermediate 1,3-dipoles.
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- Mlostoń, Grzegorz
- Kowalski, Marcin K
- Obijalska, Emilia
- Heimgartner, Heinz
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Mlostoń, G., Kowalski, M. K., Obijalska, E., & Heimgartner, H. (2017). Efficient synthesis of fluoroalkylated 1,4,2-oxathiazoles via regioselective [3 + 2]-cycloaddition of fluorinated nitrile oxides with thioketones. Journal of Fluorine Chemistry, 199, 92–96. https://doi.org/10.1016/j.jfluchem.2017.04.011
