Synthesis and properties of N-(alkenylidene)trifluoromethanesulfonamides

被引：0
|
作者：
B. A. Shainyan
L. L. Tolstikova
机构：
[1] Russian Academy of Sciences,Favorskii Irkutsk Institute of Chemistry, Siberian Branch
来源：
Russian Journal of Organic Chemistry | 2016年 / 52卷
关键词：
Trifluoro; Methanesulfonamide; Quantum Chemical Analysis; Trifluoromethanesulfonamide; Initial Aldehyde;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
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.
引用
收藏
页码：499 / 502
页数：3
相关论文
共 26 条
  • [1] Synthesis and properties of N-(alkenylidene)trifluoromethanesulfonamides
    Shainyan, B. A.
    Tolstikova, L. L.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (04) : 499 - 502
  • [2] Synthesis and structure of N-(diaminomethylidene)- and N-[bis(cyclohexylamino)methylidene]trifluoromethanesulfonamides
    L. L. Tolstikova
    N. N. Chipanina
    L. P. Oznobikhina
    B. A. Shainyan
    Russian Journal of Organic Chemistry, 2011, 47 : 1278 - 1283
  • [3] Reactions of N-(Polychloroethylidene)arene-and - trifluoromethanesulfonamides with indoles
    E. V. Kondrashov
    E. V. Rudyakova
    I. B. Rozentsveig
    I. V. Ushakova
    G. N. Rozentsveig
    V. A. Savosik
    K. A. Chernyshev
    L. B. Krivdin
    G. G. Levkovskaya
    Russian Journal of Organic Chemistry, 2008, 44 : 86 - 94
  • [4] Reactions of N-(polychloroethylidene)arene- and -trifluoromethanesulfonamides with indoles
    Kondrashov, E. V.
    Rudyakova, E. V.
    Rozentsveig, I. B.
    Ushakova, I. V.
    Rozentsveig, G. N.
    Savosilk, V. A.
    Chernyshev, K. A.
    Krivdin, L. B.
    Levkovskaya, G. G.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 44 (01) : 86 - 94
  • [5] Synthesis and properties of N-(allyl)trifluoromethanesulfonamide
    B. A. Shainyan
    Yu. S. Danilevich
    Russian Journal of Organic Chemistry, 2013, 49 : 922 - 923
  • [6] Synthesis and properties of N-(allyl)trifluoromethanesulfonamide
    Shainyan, B. A.
    Danilevich, Yu S.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 49 (06) : 922 - 923
  • [7] Synthesis of N-(2,2-Dichloroethylidene)trifluoromethanesulfonamide
    I. B. Rozentsveig
    E. V. Kondrashov
    G. G. Levkovskaya
    A. N. Mirskova
    Russian Journal of Organic Chemistry, 2001, 37 : 739 - 739
  • [8] Synthesis of N-(2,2-dichloroethylidene)trifluoromethanesulfonamide
    Rozentsveig, IB
    Kondrashov, EV
    Levkovskaya, GG
    Mirskova, AN
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 37 (05) : 739 - 739
  • [9] N-(Trimethylsilylmethyl)trifluoromethanesulfonamide
    Suslova, E. N.
    Shainyan, B. A.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2012, 82 (07) : 1311 - 1312
  • [10] N-(Trimethylsilylmethyl)trifluoromethanesulfonamide
    E. N. Suslova
    B. A. Shainyan
    Russian Journal of General Chemistry, 2012, 82 : 1311 - 1312
123