rac-2-[(diphenylphosphanyl)methyl]ferrocenecarboxylic acid | 867061-27-6

• 英文名称: rac-2-[(diphenylphosphanyl)methyl]ferrocenecarboxylic acid
• 英文别名: rac-[2-(diphenylphosphanyl)methyl]ferrocenecarboxylic acid；rac-2-((diphenylphosphino)methyl)ferrocenecarboxylic acid
• CAS: 867061-27-6
• 化学式: C₂₄H₂₁FeO₂P
• 分子量: 428.25
• InChiKey: POXMBSQAYWICLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 rac-2-[(diphenylphosphanyl)methyl]ferrocenecarboxylic acid 以 四氢呋喃 、 乙醚 为溶剂， 以98%的产率得到methyl rac-2-[(diphenylphosphino)methyl]ferrocenecarboxylate
  参考文献：
  名称：

  Synthesis and structural characterization of rac-2-[(diphenylphosphino)methyl]ferrocenecarboxylic acid, its selected derivatives and some rhodium complexes

  摘要：

  rac-2-[(Diphenylphosphino)methyl]ferrocenecarboxylic acid (1) was prepared in a good yield from rac-2-(N,N-dimethylaminomethyl)bromoferrocene (2) via rac-2-(hydroxymethyl)bromoferrocene (4) and rac-2-[(diphenylphosphino)methyl]bromoferrocene (5), and further converted to the respective phosphine oxide (6), phosphine sulfide (7) and methyl ester (8). The phosphines 1 and 8 were studied as ligands in rhodium complexes. The reaction of di-mu-chloro-bis[chloro-(eta(5)-pentamethylcyclopentadienyl)rhodium(III)] with the stoichiometric amounts of 1 and 8 yielded the corresponding mononuclear complexes with P-monodentate ligands: [RhCl2,(eta(5)-C5Me5)(L-kappa P)], 9 and 10, respectively. Attempted deprotonation of 9 with LiBu or KOt-Bu gave intractable mixtures, in which the parent complex 9 as the major component was accompanied by two new compounds, likely the diastereoizomeric phosphinocarboxylate complexes. A defined O,P-chelating phosphinocarboxylate complex, [SP-4-2]-carbonyl-[rac-2-{(diphenylphosphino)methyl}ferrocenecarboxylato-kappa O-2,P]-tricyclohexylphosphinerhodium(I) (12), was obtained from the displacement of acetylacetonate(1-) (acac) ligand in [Rh(acac)(CO)(PCy3)] (Cy = cyclohexyl) with acid 1. The structures of 1, 6 - CHCl3, and 7 - 1/2CH(2)Cl(2), 10, and hydrated complexes 9 and 12 were determined by single-crystal X-ray diffraction. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.06.035
• 作为产物：
  描述：

  rac-2-[(diphenylphosphino)methyl]bromoferrocene 、 二氧化碳 在 正丁基锂 作用下， 以 not given 为溶剂， 生成 rac-2-[(diphenylphosphanyl)methyl]ferrocenecarboxylic acid
  参考文献：
  名称：

  The Chemistry of Phosphanyl‐ferrocenecarboxylic Ligands

  摘要：

  AbstractThe chemistry of ferrocene attracts considerable research interest even more than 50 years after its discovery, being stimulated mainly by applications of ferrocene ligands in catalysis. To the present day, the design of new ferrocene compounds ensued—sometimes by serendipity—the preparation of unprecedented coordination compounds and organometallic materials and, in the case of ferrocene compounds containing appropriate donor sets, led to numerous successful catalytic systems. This review provides a systematic survey of the chemistry of phosphanyl‐ferrocenecarboxylic ligands as a specific class of hybrid ferrocene ligands that emerged about ten years ago, illustrating their synthesis, coordination behaviour, and catalytic applications. Attention is also paid to the structural chemistry of these functional ferrocene ligands. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  DOI：

  10.1002/ejic.200500485

文献信息

• Palladium(II) Complexes with Phosphanylferrocenecarboxylate Ligands and Their Use as Catalyst Precursors for Semialternating CO–Ethylene Copolymerization
  作者：Claudio Bianchini、Andrea Meli、Werner Oberhauser、Anna Maria Segarra、Elisa Passaglia、Martin Lamač、Petr Štěpnička

  DOI：10.1002/ejic.200700903

  日期：2008.1

  which, however, regenerates catalytically active PdII–H species by reaction with TsOH and that β-chelates of the formula [Pd(CH2CH2C(O)P)(S)(κP-P~OH)]OTs (P = propagating polyketone chain) are catalyst resting states. For the first time, β-chelate propagating species have been intercepted in a CO–olefin copolymerization assisted by catalysts devoid of a chelating ligand. (© Wiley-VCH Verlag GmbH &

  合成了中性 [Pd(κP,κO-P~O)(κ3C,C,C-碳环烯基)] 配合物，其中 P~O 是手性或非手性螯合膦酰二茂铁羧酸配体，并通过多核 NMR 光谱进行表征。代表性复合物的晶体结构通过单晶 X 射线衍射分析确定。在所有配合物中，钯 (II) 离子位于由阴离子 P~O- 配体的 P 和 O 供体原子、σ-碳原子和来自 a 的 C-C 双键形成的方形平面的中心。碳环烯基配体。还合成并表征了具有式[PdCl(Me)(κP,κH-P~OH)]和[Pd(Me)(OTs)(κP,κH-P~OH)]的中性甲基配合物。根据 IR、NMR 和 MS-FAB 数据，建议将甲基配合物配制成第四个配位位置，该位置由游离羧酸部分 [P~OH = 1'-(二苯基膦基)二茂铁羧酸]或溶剂分子的兴奋性 O-H...Pd 相互作用占据。在过量的对甲苯磺酸存在下，选定的配合物被用作 CO-乙烯在甲醇中共聚的催化剂前体