Lithium;1,2,3,4,5-pentakis-phenyl-1-silanidacyclopenta-2,4-diene | 667456-59-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: Lithium;1,2,3,4,5-pentakis-phenyl-1-silanidacyclopenta-2,4-diene
• 英文别名: lithium;1,2,3,4,5-pentakis-phenyl-1-silanidacyclopenta-2,4-diene
• CAS: 667456-59-9
• 化学式: C₃₄H₂₅Si*Li
• 分子量: 468.599
• InChiKey: YNGYOFKWTPNSCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  6.0
• 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：

  1-chloro-1,2,3,4,5-pentaphenylsilole 在 lithium 作用下， 以 四氢呋喃 为溶剂， 生成 1,1,2,3,4,5-六苯基噻咯 、 、 Lithium;1,2,3,4,5-pentakis-phenyl-1-silanidacyclopenta-2,4-diene
  参考文献：
  名称：

  Reduction of 1-chloro-1,2,3,4,5-pentaphenylsilole: formation of silole monoanion and dianion

  摘要：

  The reduction of 1-chloro-1,2,3,4,5-pentaphenylsilole, (C4Ph4SiPhCl, 1) with 2 equiv lithium gave the pentaphenylsilole anion [C4Ph4SiPh](-) (2), silole dianion [C4Ph4Si](2-) (3), and hexaphenylsilole C4Ph4SiPh2, (4). 2, 3, and 4 from the reaction mixture were characterized by Si-29 NMR spectroscopy. The Si-29 chemical shift of 3.7 ppm for 2 is shifted upfield as compared to that of previously reported t-butyltetraphenyisilole anion Li[C(4)Ph(4)SitBu], but shifted downfield compared to that of the other silole monoanion such as Li[C4Me4SiSiMe3], indicating the delocalization of silole anion through the 5-membered ring. Derivatization of the reaction mixture with iodomathane gave C4Ph4SiPh2 (4), C4Ph4SiMePh (5), and C4Ph4SiMe2 (6), which were characterized by H-1, C-13, and 29 Si NMR spectroscopy. The silole dianion 3 could be either from the continuous reduction of I with lithium or from the disproportionation of 2. The reduction of I with excess lithium in THF gave the silole dianion [C4Ph4Si](2-) in about 70% yield. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2003.09.040

文献信息

• Reduction of 1-chloro-1,2,3,4,5-pentaphenylsilole: formation of silole monoanion and dianion
  作者：Honglae Sohn

  DOI：10.1016/j.jorganchem.2003.09.040

  日期：2004.1

  The reduction of 1-chloro-1,2,3,4,5-pentaphenylsilole, (C4Ph4SiPhCl, 1) with 2 equiv lithium gave the pentaphenylsilole anion [C4Ph4SiPh](-) (2), silole dianion [C4Ph4Si](2-) (3), and hexaphenylsilole C4Ph4SiPh2, (4). 2, 3, and 4 from the reaction mixture were characterized by Si-29 NMR spectroscopy. The Si-29 chemical shift of 3.7 ppm for 2 is shifted upfield as compared to that of previously reported t-butyltetraphenyisilole anion Li[C(4)Ph(4)SitBu], but shifted downfield compared to that of the other silole monoanion such as Li[C4Me4SiSiMe3], indicating the delocalization of silole anion through the 5-membered ring. Derivatization of the reaction mixture with iodomathane gave C4Ph4SiPh2 (4), C4Ph4SiMePh (5), and C4Ph4SiMe2 (6), which were characterized by H-1, C-13, and 29 Si NMR spectroscopy. The silole dianion 3 could be either from the continuous reduction of I with lithium or from the disproportionation of 2. The reduction of I with excess lithium in THF gave the silole dianion [C4Ph4Si](2-) in about 70% yield. (C) 2003 Elsevier B.V. All rights reserved.