tri(2-butyl)chlorogermane | 883983-96-8

• 分子结构分类: 有机化合物 - 有机金属化合物
• 英文名称: tri(2-butyl)chlorogermane
• 英文别名: Bu(s)3GeCl
• CAS: 883983-96-8
• 化学式: C₁₂H₂₇ClGe
• 分子量: 279.389
• InChiKey: FREGXSCAOSXDMN-SRVKXCTJSA-N

物化性质

• 沸点：
  93 °C(Press: 3 Torr)
• 密度：
  1.1242 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  14.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  tri(2-butyl)chlorogermane 以 乙腈 、 苯 为溶剂， 生成 s-Bu3GeGePh3
  参考文献：
  名称：

  ⁷³Ge NMR Spectral Investigations of Singly Bonded Oligogermanes

  摘要：

  The synthesis of the two digermanes (Bu3GeGePh3)-Ge-s and PhMe2GeGePh3, as well as the branched tetragermane PhGe(GeBu3n)(3), was achieved using the hydrogermnolysis reaction. These species were fully characterized by NMR (H-1, C-13) spectroscopy and elemental analysis, and the crystal structure of PhMe2GeGePh3 was determined. These three species, along with I I other oligogermanes, were also characterized by Ge-73 NMR spectroscopy. Chemical shifts of the Ge-73 NMR resonances for these oligogermanes have been correlated with the substitution pattern at germanium and also with the number of germanium-germanium bonds at the individual Ge centers. Germanium centers having only one attached germanium atom result in resonances appearing in the range delta -30 to -65 ppm, while those having two or three bonded germanium atoms exhibit resonances in the respective ranges delta -100 to -120 and delta -195 to -210 ppm. Chemical shifts of resonances for germanium centers bearing phenyl substituents appear upfield from those having alkyl substituents.

  DOI：

  10.1021/om900035r
• 作为产物：
  描述：

  仲丁基氯化镁 、 四氯化锗 以 乙醚 为溶剂， 以27%的产率得到tri(2-butyl)chlorogermane
  参考文献：
  名称：

  ⁷³Ge NMR Spectral Investigations of Singly Bonded Oligogermanes

  摘要：

  The synthesis of the two digermanes (Bu3GeGePh3)-Ge-s and PhMe2GeGePh3, as well as the branched tetragermane PhGe(GeBu3n)(3), was achieved using the hydrogermnolysis reaction. These species were fully characterized by NMR (H-1, C-13) spectroscopy and elemental analysis, and the crystal structure of PhMe2GeGePh3 was determined. These three species, along with I I other oligogermanes, were also characterized by Ge-73 NMR spectroscopy. Chemical shifts of the Ge-73 NMR resonances for these oligogermanes have been correlated with the substitution pattern at germanium and also with the number of germanium-germanium bonds at the individual Ge centers. Germanium centers having only one attached germanium atom result in resonances appearing in the range delta -30 to -65 ppm, while those having two or three bonded germanium atoms exhibit resonances in the respective ranges delta -100 to -120 and delta -195 to -210 ppm. Chemical shifts of resonances for germanium centers bearing phenyl substituents appear upfield from those having alkyl substituents.

  DOI：

  10.1021/om900035r

文献信息

• Organomagnesium Synthesis of sec-Butyl- and tert-Alkylchlorogermanes and Their Reaction with Ethynylmagnesium Bromide
  作者：O. G. Yarosh、M. G. Voronkov、L. V. Zhilitskaya、N. O. Yarosh、A. I. Albanov、I. M. Korotaeva

  DOI：10.1007/s11176-005-0305-z

  日期：2005.5

  The limits of application of organomagnesium synthesis to the substitution of chlorine atoms in tetrachlorogermane with bulky alkyl groups are established. The reaction of tetrachlorogermane with 2-butylmagnesium chloride leads to the substitution of one, two, or three chlorine atoms, yielding the corresponding alkylchlorogermanes (MeEtCH)nGeCl4-n . The reaction of GeCl4 with tert-alkylmagnesium halides leads to the substitution of only one chlorine atom, yielding tert-alkyltrichlorogermanes RMe2CGeCl3 (R = Me, Et, Bu). tert-Butyltrichlorogermane reacts with ethylmagnesium bromide to give ethyl(tert-butyl)dichlorogermane. Isopropyltrichlorogermane reacts with tert-butylmagnesium chloride to give isopropyl(tert-butyl)dichlorogermane. This shows that the organomagnesium synthesis does allow linking of two bulky substituents to the germanium atom. The reaction of tert-alkyltrichlorogermanes and 2-butyltrichlorogermane in THF with ethynylmagnesium bromide, in which the hydrocarbon group is the most sterically accessible, allows substitution of all the three chlorine atoms, yielding the corresponding alkyl(triethynyl)germanes. The latter compounds react with the Grignard reagent and trimethylchlorosilane to give the corresponding alkyl(trimethylsilylethynyl)germanes.

  有机镁合成在用笨重的烷基取代四氯锗烷中氯原子的应用范围已被确立。四氯锗烷与2-丁基镁氯反应能够替代一个、两个或三个氯原子，生成相应的烷基氯锗烷（MeEtCH）nGeCl4-n。四氯锗（GeCl4）与叔烷基镁卤化物反应仅能替代一个氯原子，生成叔烷基三氯锗烷RMe2CGeCl3（R = Me，Et，Bu）。叔丁基三氯锗与溴化乙基镁反应生成乙基（叔丁基）二氯锗烷。异丙基三氯锗与叔丁基镁氯反应生成异丙基（叔丁基）二氯锗烷。这个结果表明，有机镁合成确实允许在锗原子上连接两个笨重的取代基。在THF中，叔烷基三氯锗与2-丁基三氯锗与乙炔基镁溴反应，其中碳氢基团是最易获得的空间位阻团，能够替代所有三个氯原子，生成相应的烷基（三乙炔基）锗烷。后者化合物与格里尼亚试剂和三甲基氯硅烷反应生成相应的烷基（三甲基硅乙炔基）锗烷。