N-Fluorotrifluoromethylsulfonylamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-Fluorotrifluoromethylsulfonylamide
• 英文别名: N,1,1,1-tetrafluoromethanesulfonamide
• 化学式: CHF₄NO₂S
• 分子量: 167.084
• InChiKey: LYRAOXOETGHQHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  Tetrabutylammonium N-fluorotrifluoromethylsulfonylamide 在 硫酸 作用下， 反应 0.17h， 以41%的产率得到N-Fluorotrifluoromethylsulfonylamide
  参考文献：
  名称：

  N-Fluoro-bis[(trifluoromethyl)sulfonyl]imide: interesting reactions involving nucleophilic attack on sulfonyl groups

  摘要：

  N-Fluoro-bis[(trifluoromethyl)sulfonyl]imide (1) undergoes reaction with a variety of nucleophiles to give a number of interesting products. Under suitable conditions, the sulfonyl group on 1 is subject to nucleophilic attack forming N-fluoro-trifluoromethylsulfonyl amide (3) and Nu-SO2CF3. Surprisingly, 3 can also function as a weak nucleophile in the absence of other stronger bases. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(99)00231-6

文献信息

• N-Fluorobis[(perfluoroalkyl)sulfonyl]imides: reactions with some olefins via .alpha.-fluoro carbocationic intermediates
  作者：Darryl D. DesMarteau、Ze Qi Xu、Michael Witz

  DOI：10.1021/jo00028a042

  日期：1992.1

  N-Fluorobis(perfluoroalkyl)sulfonyl]imides are a new class of electrophilic fluorinating agents. Reaction of (CF3SO2)2NF (1) with olefins gave various products, depending on the reaction conditions and the structure of the substrate. In solvents of higher nucleophilicity such as H2O, acetic acid, aqueous HCl, and (HF)(n)Py, alpha-fluorohydrins or their acetates, alpha,beta-chlorofluoro- and alpha,beta-difluoroalkanes were obtained. In acetic acid, trans-stilbene and tetraphenylethylene produced the rearranged, nonfluorinated aldehyde and ketone. Evidence is presented for the reactions proceeding via a one-electron transfer mechanism involving alpha-fluorocarbocationic intermediates.
• N-Fluoro-bis[(trifluoromethyl)sulfonyl]imide: interesting reactions involving nucleophilic attack on sulfonyl groups
  作者：Weiwen Ying、Darryl D. DesMarteau、Ze-Qi Xu、Michael Witz

  DOI：10.1016/s0022-1139(99)00231-6

  日期：2000.3

  N-Fluoro-bis[(trifluoromethyl)sulfonyl]imide (1) undergoes reaction with a variety of nucleophiles to give a number of interesting products. Under suitable conditions, the sulfonyl group on 1 is subject to nucleophilic attack forming N-fluoro-trifluoromethylsulfonyl amide (3) and Nu-SO2CF3. Surprisingly, 3 can also function as a weak nucleophile in the absence of other stronger bases. (C) 2000 Elsevier Science S.A. All rights reserved.