1,1'-bis(pentafluorophenyl)ferrocene | 55517-82-3

• 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: 1,1'-bis(pentafluorophenyl)ferrocene
• 英文别名: bis[η(5)-(pentafluorophenyl)cyclopentadienyl]iron(II)；5-cyclopenta-2,4-dien-1-ylidene-1,2,3,4,6-pentafluorocyclohexa-1,3-diene;1-cyclopenta-2,4-dien-1-yl-2,3,4,5,6-pentafluorobenzene;iron(2+)
• CAS: 55517-82-3
• 化学式: C₂₂H₈F₁₀Fe
• 分子量: 518.137
• InChiKey: LHKMVVHHUYTWSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.53
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  4.0
• 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：
  12

反应信息

• 作为反应物：
  描述：

  silver hexafluoroantimonate 、 1,1'-bis(pentafluorophenyl)ferrocene 以 乙醚 为溶剂， 反应 16.0h， 以55%的产率得到1,1′-bis(pentafluorophenyl)ferrocenium hexafluoroantimonate
  参考文献：
  名称：

  用于 Friedel-Crafts 烷基化和 Diels-Alder 反应的金属茂路易斯酸催化剂

  摘要：

  制备并探索了一系列二茂铁（Fc、FcCO 2 H、FcCO 2 Me 和 Fc(Me) 10）和二茂钴（Cc、CcCO 2 H、CcCO 2 Me）盐作为耐空气和耐水的均相催化剂。发现它们在室温下是反式-β-硝基苯乙烯和N-甲基吲哚的 Friedel-Crafts 烷基化以及 1,3-环己二烯与甲基乙烯基酮的 Diels-Alder 环加成的活性催化剂。这些催化剂是对更传统的路易斯酸的有价值的补充，因为它们可溶于非极性介质，不分解起始材料，并且利用路易斯（金属）和布朗斯台德酸（CO 2H) 观察到中心。

  DOI：

  10.1021/acs.organomet.2c00408
• 作为产物：
  描述：

  iron(II) bromide 、 sodium (pentafluorophenyl)cyclopentadienide 以 四氢呋喃 为溶剂， 以86%的产率得到1,1'-bis(pentafluorophenyl)ferrocene
  参考文献：
  名称：

  Synthesis of Pentafluorophenyl-Substituted Cyclopentadienes and Their Use as Transition-Metal Ligands

  摘要：

  The reaction of NaC5H5 (NaCp) and hexafluorobenzene (1:1 ratio) in THF at 25 degrees C for 15 h afforded, after hydrolysis, a mixture of regioisomeric (pentafluorophenyl)cyclopentadienes. This mixture was isolated as a monoisomeric dimer of 1-(pentafluorophenyl)cyclopentadiene. The structure of the dimer was determined crystallographically. Flash vacuum thermolytic cracking of the dimer at 200 degrees C regenerated (pentafluorophenyl)cyclopentadiene as a mixture of regioisomers. In contrast, the reaction of NaCp, NaH, and C6F6 (1:2:5 ratio) in THF at reflux for 3 d affords, after hydrolysis, 1,4-bis(pentafluorophenyl)cyclopentadiene which does not dimerize. Either the mono- or the disubsubstituted diene reacts with NaH in THF;to afford the corresponding stable substituted sodium cyclopentadienides in high yields. Sodium (pentafluorophenyl)cyclopentadienide, (C6F5)C5H4Na, reacted with FeBr2, Re(CO)(5)Br, and ZrCl4(THF)(2), to afford the transition metal complexes (eta(5)-C5H4C6F5)(2)Fe, (eta(5)-C6H4C6F5)Re(CO)(3), and (eta(5)-C5H4C6F5)(2)ZrCl2. Sodium 1,3-bis(pentafluorophenyl)cyclopentadienide reacted with FeBr2 and Re(CO)(5)Br to give the corresponding complexes [eta(5)-1,3-C5H3(C6F5)(2)]Fe-2 and [eta(5)-1,3-C5H3(C6F5)(2)]Re(CO)(3). Infrared spectroscopic analysis of the tricarbonylrhenium(I) complexes and cyclic voltammetric analysis of the substituted ferrocenes quantified the strong electron-withdrawing effects of the pentafluorophenyl substituents.

  DOI：

  10.1021/om9608216

文献信息

• Synthesis and Structural Trends in Pentafluorophenyl-Substituted Ferrocenes, 1,4-Tetrafluorophenylene-Linked Diferrocenes, and 1,1‘-Ferrocenylene−1,4-Tetrafluorophenylene Co-oligomers
  作者：Paul A. Deck、Michael J. Lane、Jennifer L. Montgomery、Carla Slebodnick、Frank R. Fronczek

  DOI：10.1021/om990930v

  日期：2000.3.1

  [1-(C6F5)-2-RNCp]FeCp (7). Complex 6 reacts with 0.5 equiv of C6F6 to afford CpFe[2-RNCp](1,4-C6F4)[2-RNCp]FeCp as a mixture of two diastereomers (meso-8, major and dl-8, minor). The relative stereochemistry of meso-8 is established by crystallographic analysis of the corresponding bis(methiodide) (12). [1-Li-2-RNCp]Fe(CpLi) (9) reacts with excess C6F6 to afford mainly the diarylated ferrocene [1-(C6F5)-2-RNCp]Fe(CpC6F5)

  1,1'-二硫代二茂铁或（CpLi）2 Fe（1）与过量的C 6 F 6在THF中反应生成大部分（C 6 F 5 Cp）2 Fe（2），并伴有二铁配合物（C 6 F 5 Cp）FeCp（1，4-C 6 F 4）CpFe（CpC 6 F 5）（3）。的反应1与1.0当量的C 6 ˚F 6次得到的分配给微溶的逐步增长的低聚物的混合物[-FeCp（1,4-C 6 ˚F 4） - ] Ñ（4）。[1-Li-2-R N Cp] FeCp（6，R N = CH 2 NMe 2）与1当量的C 6 F 6反应得到[1-（C 6 F 5）-2-R N Cp] FeCp（7）。配合物6与0.5当量的C 6 F 6反应，得到CpFe [2-R N Cp]（1,4-C 6 F 4）[2-R N Cp] FeCp，为两种非对映体的混合物（meso -8，少校和dl -8， 次要的）。meso- 8的相对立体化学是通