2,4-N,N-trifluorophenyl-1,3-tetramesitylcyclogermazane | 169053-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,4-N,N-trifluorophenyl-1,3-tetramesitylcyclogermazane
• 英文别名: 1,3-Bis(2,4,6-trifluorophenyl)-2,2,4,4-tetrakis(2,4,6-trimethylphenyl)-1,3,2,4-diazadigermetidine
• CAS: 169053-38-7
• 化学式: C₄₈H₄₈F₆Ge₂N₂
• 分子量: 912.093
• InChiKey: ZKDRRMIYKVNQDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.06
• 重原子数：
  58
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,4-N,N-trifluorophenyl-1,3-tetramesitylcyclogermazane 、 水 以 水 为溶剂， 生成 dimesitylgermanediol 、
  参考文献：
  名称：

  DERIVES N-GERMANIES DE LA 2,4,6-TRIFLUOROANILINE: GERMYLAMINES, GERMA-IMINE, CYCLODIGERMAZANE

  摘要：

  Germyl derivatives of N-2,4,6-trifluoroaniline were synthesized either by dehydrohalogenation between halogermanes and 2,4,6-trifluoroaniline over DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) or by elimination between halogermanes and 2,4,6-trfluoroanilinolithium. Dimesitylfluorogermyl N-2,4,6-trifluoroanilinolithium stabilized by THF slowly eliminated lithium fluoride leading to 2,4(2,4,6-trifluorophenyl)-1,3-tetramesitylcyclodigermazane, mainly through intermolecular elimination while in the presence of MgBr2 or tBuMgBr the corresponding germa-imine was formed. Dimesitylchlorogermyl-2,4,6-tritluoroanilino lithium also led to cyclodigermazane while the corresponding bromogermyl lithium or magnesium compound gave mainly the stable 2,4,6-trifluorophenyl dimesitylgerma-imine by intramolecular elimination. The same stable germa-imine was also obtained by exchange reaction between dichlorodimesitylgermane and N-bis(triethylgermyl)2,4,6-trifluoroaniline. Reactivities of monomeric germa-imine and its dimer cyclodigermazane are compared. The dimer is almost inert towards water and methanol and does not react with chloroform and N-tert-butylphenyl nitrone while the germa-imine leads to the corresponding adducts. The adduct with chloroform through alpha-elimination of dichlorocarbene gave N-dimesitylchlorogermyl trifluoroaniline. The electron withrawing effects of the trifluorophenyl group on nitrogen stabilize the germa-imine, preventing its dimerization, but also induce a decrease in reactivity of germanium nitrogen compounds within the series.

  DOI：

  10.1080/10426509608046364
• 作为产物：
  描述：

  N-dimesitylfluoroogermyl N-2,4,6-trifluoroanilinolithium *3THF 以 苯 为溶剂， 以67%的产率得到2,4-N,N-trifluorophenyl-1,3-tetramesitylcyclogermazane
  参考文献：
  名称：

  DERIVES N-GERMANIES DE LA 2,4,6-TRIFLUOROANILINE: GERMYLAMINES, GERMA-IMINE, CYCLODIGERMAZANE

  摘要：

  Germyl derivatives of N-2,4,6-trifluoroaniline were synthesized either by dehydrohalogenation between halogermanes and 2,4,6-trifluoroaniline over DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) or by elimination between halogermanes and 2,4,6-trfluoroanilinolithium. Dimesitylfluorogermyl N-2,4,6-trifluoroanilinolithium stabilized by THF slowly eliminated lithium fluoride leading to 2,4(2,4,6-trifluorophenyl)-1,3-tetramesitylcyclodigermazane, mainly through intermolecular elimination while in the presence of MgBr2 or tBuMgBr the corresponding germa-imine was formed. Dimesitylchlorogermyl-2,4,6-tritluoroanilino lithium also led to cyclodigermazane while the corresponding bromogermyl lithium or magnesium compound gave mainly the stable 2,4,6-trifluorophenyl dimesitylgerma-imine by intramolecular elimination. The same stable germa-imine was also obtained by exchange reaction between dichlorodimesitylgermane and N-bis(triethylgermyl)2,4,6-trifluoroaniline. Reactivities of monomeric germa-imine and its dimer cyclodigermazane are compared. The dimer is almost inert towards water and methanol and does not react with chloroform and N-tert-butylphenyl nitrone while the germa-imine leads to the corresponding adducts. The adduct with chloroform through alpha-elimination of dichlorocarbene gave N-dimesitylchlorogermyl trifluoroaniline. The electron withrawing effects of the trifluorophenyl group on nitrogen stabilize the germa-imine, preventing its dimerization, but also induce a decrease in reactivity of germanium nitrogen compounds within the series.

  DOI：

  10.1080/10426509608046364

文献信息

• A stable germa-imine: N-2,4,6-trifluorophenyldimesitylgerma-imine; synthesis and reactivity
  作者：Monique Rivière-Baudet、Jacques Satgé、Fatima El Baz

  DOI：10.1039/c39950001687

  日期：——

  Stabilization of a germa-imine is achieved by the use of the electron-withdrawing 2,4,6-trifluorophenyl group on nitrogen.

  锗亚胺的稳定化是通过使用氮上的吸电子 2,4,6-三氟苯基来实现的。