2,4,6-trideuterofluorobenzene | 576-85-2

• 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: 2,4,6-trideuterofluorobenzene
• 英文别名: 1,3,5-trideutero-2-fluorobenzene；1-Fluor-2,4,6-tridenterio-benzol；2,4,6-D3-Fluorbenzol；Fluorbenzol-d3；1,3,5-trideuterio-2-fluoro-benzene；1,3,5-Trideuterio-2-fluor-benzol；1-Fluor-2,4,6-trideutero-benzol；1,3,5-Trideuterio-2-fluorobenzene；1,3,5-trideuterio-2-fluorobenzene
• CAS: 576-85-2
• 化学式: C₆H₅F
• 分子量: 99.0803
• InChiKey: PYLWMHQQBFSUBP-NHPOFCFZSA-N

物化性质

• 沸点：
  84.5 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,4,6-三溴苯胺 在 盐酸 、 tetrafluoroboric acid 、 重水 、 锌 、 sodium nitrite 作用下， 生成 2,4,6-trideuterofluorobenzene
  参考文献：
  名称：

  Microwave Determination of the Structure of Fluorobenzene

  摘要：

  3D-, 4D-, and 2,4,6 D3-fluorobenzene have been prepared. Their microwave spectra have been recorded and analyzed. Values of their rotational constants together with known values of the rotational constants of ordinary fluorobenzene do not suffice for an unambiguous calculation of the 11 geometrical parameters of the molecule but by assistance from valence theory a small number of fairly probable models may be pointed out.

  DOI：

  10.1063/1.1743237

文献信息

• The Mechanism of Aminations of Halobenzenes¹
  作者：John D. Roberts、Dorothy A. Semenow、Howard E. Simmons、L. A. Carlsmith

  DOI：10.1021/ja01584a024

  日期：1956.2

  An elimination-addition mechanism, probably involving a "benzyne" intermediate, has been established for the rearrangements which often occur in the conversion of non-activated aryl halides to arylamines with metallic amides. The evidence for the "benzyne" intermediate was obtained through ^(14)C-tracer studies of rearrangements with halobenzenes and experiments designed to determine the role of the

  一种消除加成机制，可能涉及“苄”中间体，已经为重排建立了重排，这种重排经常发生在用金属酰胺将未活化的芳基卤转化为芳胺的过程中。“苄”中间体的证据是通过 ^(14) C-示踪剂研究卤代苯重排和实验设计来确定位于被取代的卤素原子邻位的氢原子的作用获得的。
• Electrophilic fluorination of aromatic compounds with NF type reagents: kinetic isotope effects and mechanism
  作者：Gennady I. Borodkin、Pavel A. Zaikin、Vyacheslav G. Shubin

  DOI：10.1016/j.tetlet.2006.02.016

  日期：2006.4

  effects in fluorination of aromatic compounds with NF type reagents have been studied to reveal the reaction mechanism. The results obtained are consistent with a polar SEAr mechanism. Small deuterium isotope effects (kH/kD = 0.86–0.99) show that decomposition of a Wheland-type intermediate is not rate determining. The first example of a 1,2-hydrogen shift accompanying electrophilic fluorination of arenes

  研究了用NF型试剂对芳族化合物进行氟化时的H / D同位素效应，以揭示其反应机理。获得的结果与极性S E Ar机制一致。小氘同位素效应（k H / k D  = 0.86-0.99）表明，Wheland型中间体的分解不是决定速率的。在芳族化合物的1,3,5-三氟甲苯的氟化中已经观察到伴随芳族化合物的亲电氟化而发生的1,2-氢转移的第一个例子。
• Notes - Substitution of Halogens by Deuterium in Organic Compounds Without Undesired Exchange of Hydrogen by Deuterium
  作者：Borge Bak

  DOI：10.1021/jo01113a601

  日期：1956.7
• Mechanism of electrophilic fluorination of aromatic compounds with NF-reagents
  作者：G. I. Borodkin、P. A. Zaikin、M. M. Shakirov、V. G. Shubin

  DOI：10.1134/s1070428007100077

  日期：2007.10

  Kinetic isotope effects H/D in electrophilic fluorination of aromatic compounds with NF-reagents were investigated. The small values of k(H)/k(D) (0.86-1.00) are in agreement with the polar reaction mechanism where the Wheland complex decomposition is not the limiting stage. The fluorination of 1,3,5-trideuterobenzene was established by H-1 and F-19 NMR spectroscopy to occur with a 1,2-migration of a hydrogen (deuterium) atom. The analysis of Brown-Stock relationship demonstrated that the activity of NF-reagents exceeded that of many known electrophilic systems including halogenation, but it was essentially less than the activity of elemental fluorine.