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Synthesis and properties of N-(alkenylidene)trifluoromethanesulfonamides

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Abstract

N-Alkenylidenetrifluoromethanesulfonamides TfN=CH–CR=C(Me)R′ (R, R′ = H, Me) have been synthesized by reaction of N-sulfinyltrifluoromethanesulfonamide TfNSO with (E)-but-2-enal, (E)-2-methylbut- 2-enal, and 3-methylbut-2-enal. Despite greater stability of N-alkenylidenetrifluoromethanesulfonamides relative to their propargyl isomers TfNHCH2C≡CR, no rearrangement of the latter into the former occurs due to the presence of an acidic NH proton, which hampers formation of carbon-centered anion.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    B. A. Shainyan & L. L. Tolstikova

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  1. B. A. Shainyan
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  2. L. L. Tolstikova
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Correspondence to B. A. Shainyan.

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Original Russian Text © B.A. Shainyan, L.L. Tolstikova, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 4, pp. 511–514.

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Shainyan, B.A., Tolstikova, L.L. Synthesis and properties of N-(alkenylidene)trifluoromethanesulfonamides. Russ J Org Chem 52, 499–502 (2016). https://doi.org/10.1134/S1070428016040035

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  • DOI: https://doi.org/10.1134/S1070428016040035

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