pyridinium (trifluoromethanesulfonyl)imide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: pyridinium (trifluoromethanesulfonyl)imide
• 英文别名: pyridinium trifluoromethanesulfonylimide；Pyridin-1-ium-1-yl(trifluoromethylsulfonyl)azanide
• 化学式: C₆H₅F₃N₂O₂S
• 分子量: 226.179
• InChiKey: QJSBONDFFOTBLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  吡啶 、 [N-(trifluoromethylsulfonyl)imino][4-(trifluoromethyl)phenyl]-λ³-bromane 以 乙腈 为溶剂， 反应 0.17h， 以100%的产率得到pyridinium (trifluoromethanesulfonyl)imide
  参考文献：
  名称：

  Direct Transfer of the Sulfonylimino Group of Imino-λ³-Bromane to N-Heterocycles and Trialkylamines: Synthesis of N-Iminoammonium Ylides under Metal-Free Conditions

  摘要：

  Exposure of N-heterocycles and aliphatic trialkylamines to trifluoromethanesulfonylimino-lambda(3)-bromane at room temperature results in direct transfer of the sulfonylimino group to the nitrogen atoms and affords a variety of iminoammonium ylides under transition-metal-free conditions. The imino-lambda(3)-bromane probably serves as an active nitrenoid species without any activation and produces the ammonium ylides via a bimolecular nucleophilic substitution process.

  DOI：

  10.1021/ol802383f

文献信息

• Study on the reactions of fluoroalkanesulfonyl azides with pyridine and its derivatives
  作者：Yong Xu、Shizheng Zhu

  DOI：10.1016/s0040-4020(99)00856-x

  日期：1999.11

  The thermal reactions of fluoroalkanesutfonyl azides RfSO2N3 with pyridine and its derivatives have been investigated in detail. In many cases ,N-fluoroalkanesulfonyl pyridinium imides Y+-N−SO2Rf(Y: pyridine, 3-picoline 3,5-lutidine and quinoline) and the hydrogen abstraction products RfSO2NH2 were obtained. 2-Picoline and 4-picoline reacted with to give RfSO2NH2 exclusively. Interestingly in the reaction

  已经详细研究了氟代链烷磺酰氟叠氮化物R f SO 2 N 3与吡啶及其衍生物的热反应。在许多情况下，获得了N-氟烷磺酰基吡啶鎓酰亚胺Y + -N - SO 2 R f（Y：吡啶，3-甲基吡啶3,5-二甲基吡啶和喹啉）和氢提取产物R f SO 2 NH 2。2-甲基吡啶和4-甲基吡啶与之反应，仅得到R f SO 2 NH 2。有趣的是叠氮化物IC 2 F的反应用4-吡啶啉或喹啉在4 OC 2 F 4 SO 2 N 3中，将叠氮化物的ω-碘取代而形成ArC 2 F 4 OC 2 F 4 SO 2 NH 2。
• Direct Transfer of the Sulfonylimino Group of Imino-λ³-Bromane to <i>N</i>-Heterocycles and Trialkylamines: Synthesis of <i>N</i>-Iminoammonium Ylides under Metal-Free Conditions
  作者：Masahito Ochiai、Yufuko Kawano、Takao Kaneaki、Norihiro Tada、Kazunori Miyamoto

  DOI：10.1021/ol802383f

  日期：2009.1.15

  Exposure of N-heterocycles and aliphatic trialkylamines to trifluoromethanesulfonylimino-lambda(3)-bromane at room temperature results in direct transfer of the sulfonylimino group to the nitrogen atoms and affords a variety of iminoammonium ylides under transition-metal-free conditions. The imino-lambda(3)-bromane probably serves as an active nitrenoid species without any activation and produces the ammonium ylides via a bimolecular nucleophilic substitution process.