bis(2,4,6-trifluorophenyl) sulfoxide | 132260-87-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis(2,4,6-trifluorophenyl) sulfoxide
• 英文别名: 1,3,5-Trifluoro-2-(2,4,6-trifluorophenyl)sulfinylbenzene
• CAS: 132260-87-8
• 化学式: C₁₂H₄F₆OS
• 分子量: 310.22
• InChiKey: KECSBJPDRWKYJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1,3,5-三氟苯 在 五氟化锑 、 氟磺酸 作用下， 以 1,1,2-三氯三氟乙烷（CFC-113） 为溶剂， 以10%的产率得到bis(2,4,6-trifluorophenyl) sulfoxide
  参考文献：
  名称：

  Reaction of simple arenes with FSO3H.cntdot.SbF5/SO2: one-pot synthesis of aromatic sulfoxides. Mechanistic aspects and synthetic utility

  摘要：

  In a simple one-pot reaction, mono-, di-, tri-, and polyalkylbenzenes, isomeric alkylhalobenzenes, and fluoro-, (trifluoromethyl)-, and 1,3,5-trifluorobenzene were converted to their corresponding diaryl sulfoxides with FSO3H.SbF5 (1:1) (magic acid)/SO2. Dependency of the yields on the acidity (H0) and the arene structure was demonstrated. Reduction of the formed sulfoxide was also observed as a minor pathway to give diaryl sulfide. The reduction is superacid-catalyzed, and protonated sulfoxides are the key intermediates en route to sulfides. Protonation of several functionalized diaryl sulfoxides was also studied in magic acid/SO2 under stable ion conditions. Unlike the parent diphenyl sulfoxide, which is S-protonated, alkyl-, fluoro-, and trifluoromethyl-substituted diaryl sulfoxides O-protonate to give long-lived sulfoxonium ions. The proposed mechanism for the arene/superacid/SO2 system involves sulfination of the arenium ions, O-protonation of the resulting sulfinic acid, dehydration of the oxonium ion ''ArSO+'' and arylation. In the absence of SO2, the fluorosulfonation, ionization, arylation path becomes dominant. The scope of the reaction is sufficiently broad to be synthetically useful. The methodology is also applicable to unsymmetrical (mixed) diaryl sulfoxides.

  DOI：

  10.1021/jo00005a037

文献信息

• LAALI, KENNETH KHOSROW;NAGVEKAR, DEVDATT S., J. ORG. CHEM., 56,(1991) N, C. 1867-1874
  作者：LAALI, KENNETH KHOSROW、NAGVEKAR, DEVDATT S.

  DOI：——

  日期：——
• Reaction of simple arenes with FSO3H.cntdot.SbF5/SO2: one-pot synthesis of aromatic sulfoxides. Mechanistic aspects and synthetic utility
  作者：Kenneth Khosrow Laali、Devdatt S. Nagvekar

  DOI：10.1021/jo00005a037

  日期：1991.3

  In a simple one-pot reaction, mono-, di-, tri-, and polyalkylbenzenes, isomeric alkylhalobenzenes, and fluoro-, (trifluoromethyl)-, and 1,3,5-trifluorobenzene were converted to their corresponding diaryl sulfoxides with FSO3H.SbF5 (1:1) (magic acid)/SO2. Dependency of the yields on the acidity (H0) and the arene structure was demonstrated. Reduction of the formed sulfoxide was also observed as a minor pathway to give diaryl sulfide. The reduction is superacid-catalyzed, and protonated sulfoxides are the key intermediates en route to sulfides. Protonation of several functionalized diaryl sulfoxides was also studied in magic acid/SO2 under stable ion conditions. Unlike the parent diphenyl sulfoxide, which is S-protonated, alkyl-, fluoro-, and trifluoromethyl-substituted diaryl sulfoxides O-protonate to give long-lived sulfoxonium ions. The proposed mechanism for the arene/superacid/SO2 system involves sulfination of the arenium ions, O-protonation of the resulting sulfinic acid, dehydration of the oxonium ion ''ArSO+'' and arylation. In the absence of SO2, the fluorosulfonation, ionization, arylation path becomes dominant. The scope of the reaction is sufficiently broad to be synthetically useful. The methodology is also applicable to unsymmetrical (mixed) diaryl sulfoxides.