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Synthesis and bromination/dehydrobromination of N,N-diallyltrifluoromethanesulfonamide

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Abstract

The reaction of triflluoromethanesulfonamide with allyl bromide in dimethyl sulfoxide gave N,N-diallyltrifluoromethanesulfonamide which was subjected to bromination with 1 and 2 equiv of bromine. The product of bromine addition to both allyl groups, CF3SO2N(CH2CHBrCH2Br)2, was found to exist as a mixture of two diastereoisomers at a ratio of 9: 11. Its dehydrobromination by the action of sodium methoxide was chemoselective with successive elimination of one, two, and three hydrogen bromide molecules to afford N-(2-bromoprop-2-en-1-yl)-N-(2,3-dibromopropyl)trifluoromethanesulfonamide, N,N-bis(2-bromoprop-2-en-1-yl)trifluoromethanesulfonamide, and N-(2-bromoprop-2-en-1-yl)-N-(propadienyl)trifluoromethanesulfonamide, respectively.

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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, Yu. S. Danilevich & I. A. Ushakov

Authors
  1. B. A. Shainyan
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  2. Yu. S. Danilevich
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  3. I. A. Ushakov
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Correspondence to B. A. Shainyan.

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Original Russian Text © B.A. Shainyan, Yu.S. Danilevich, I.A. Ushakov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 12, pp. 1747–1751.

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Shainyan, B.A., Danilevich, Y.S. & Ushakov, I.A. Synthesis and bromination/dehydrobromination of N,N-diallyltrifluoromethanesulfonamide. Russ J Org Chem 52, 1738–1742 (2016). https://doi.org/10.1134/S1070428016120046

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  • DOI: https://doi.org/10.1134/S1070428016120046

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