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N-benzyl-N-[(E)-2-phenylethenyl]trifluoromethanesulfonamide

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Abstract

In the search for an approach to N-vinyltriflamides with a free NH group TfNHCH=CHR (Tf = CF3SO2) N-(benzyl)-N-(2-bromo-2-phenylethenyl)triflamide TfN(Bn)CH=CHPh was synthesized through bromination-dehydrobromination of N-(benzyl)-N-(2-phenylethyl)triflamide. At removing the benzyl protecttion by the action of trifluoromethanesulfonic acid benzyl alcohol separated; however instead of the target N-styryltriflamide unexpectedly the product of its hydrogenation was obtained, N-(2-phenylethyl)triflamide. Obviously, the benzyl alcohol was the hydrogen donor, and the easy hydrogenation was facilitated by the high electrophilicity of the double bond in N-styryltriflamide because of strong electron-acceptor effect of the triflyl group.

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References

  1. Shainyan, B.A., and Tolstikova, L.L. Chem. Rev., 2013, vol. 113, p. 699.

    Article  CAS  Google Scholar 

  2. Shainyan, B.A., Moskalik, M.Yu., Starke, I., and Schilde, U., Tetrahedron, 2010, vol. 66, p. 8383.

    Article  CAS  Google Scholar 

  3. Shainyan, B.A., and Danilevich, Yu.S., Russ. J. Org. Chem., 2013, vol. 49, p. 922.

    Article  CAS  Google Scholar 

  4. Shainyan, B.A., and Danilevich, Yu.S., Russ. J. Org. Chem., 2013, vol. 49, p. 1112.

    Article  CAS  Google Scholar 

  5. Shainyan, B.A., Chipanina, N.N., Oznobikhina, L.P., and Danilevich, Yu.S., J. Phys. Org. Chem., 2013, vol. 26, p. 653.

    Article  CAS  Google Scholar 

  6. Shainyan, B.A., and Ushakova, I.V., Russ. J. Org. Chem., 2012, vol. 48, p. 141.

    Article  CAS  Google Scholar 

  7. Ushakova, I.V., and Shainyan B.A., Russ. J. Org. Chem., 2013, vol. 49, p. 924.

    Article  CAS  Google Scholar 

  8. Chipanina, N.N., Oznobikhina, L.P., Ushakova, I.V., and Shainyan, B.A., Russ. J. Org. Chem., 2013, vol. 49, p. 999.

    Article  CAS  Google Scholar 

  9. Shainyan, B.A., and Mirskova, A.N., Russ. Chem. Rev., 1979, vol. 48, p. 107.

    Article  Google Scholar 

  10. Shainyan, B.A., and Sterkhova I.V., Russ. J. Org. Chem., 2010, vol. 46, p. 1743.

    Article  CAS  Google Scholar 

  11. Vitali, R., Caccia, G., and Gardi, R., J. Org. Chem., 1972, vol. 33, p. 3745.

    Article  Google Scholar 

  12. Liu, Z.S., and Rempel, G.L., Can. J. Chem. Eng., 2010, vol. 88, p. 376.

    CAS  Google Scholar 

  13. Yamashita, K., Nagashima, Y., Yamamoto, Y., and Nishiyama, H., Chem. Commun., 2011, p. 11552.

    Google Scholar 

Download references

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Authors and Affiliations

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

    B. A. Shainyan & I. V. Ushakova

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  1. B. A. Shainyan
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  2. I. V. Ushakova
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Correspondence to B. A. Shainyan.

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Original Russian Text © B.A. Shainyan, I.V. Ushakova, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 8, pp. 1112–1115.

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Shainyan, B.A., Ushakova, I.V. N-benzyl-N-[(E)-2-phenylethenyl]trifluoromethanesulfonamide. Russ J Org Chem 50, 1093–1096 (2014). https://doi.org/10.1134/S1070428014080041

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  • DOI: https://doi.org/10.1134/S1070428014080041

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