9-azido-9-borafluorene | 1226990-09-5

• 英文名称: 9-azido-9-borafluorene
• CAS: 1226990-09-5
• 化学式: C₃₆H₂₄B₃N₉
• 分子量: 615.08
• InChiKey: BJUBOJBNNHGZAZ-UHFFFAOYSA-N

计算性质

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

反应信息

• 作为反应物：
  描述：

  9-azido-9-borafluorene 、 水 在 air 作用下， 以 neat (no solvent) 为溶剂， 生成 tris(2-biphenylyl)boroxine
  参考文献：
  名称：

  Synthesis and Structural Characterization of 9-Azido-9-Borafluorene: Monomer and Cyclotrimer of a Borole Azide

  摘要：

  The reaction of 2,2'-dilithiobiphenyl, generated from 2,2'-dibromobiphenyl and n-BuLi, with BCl3 using n-hexane as solvent provides a high-yielding, simple preparative route to 9-chloro-9-borafluorene la. This in turn can be reacted with trimethylsilyl azide to yield 9-azido-9-borafluorene 2. Compound 2 exists as a cyclic trimer in the solid state, but in dichloromethane solution the monomer can coexist with the trimer. Azide 2 is rather unstable both in the solid state and in solution, and it transforms with trace amounts of water and oxygen to the 1,3,5-tris(2-biphenylyl)cyclotriboroxane that was characterized by X-ray diffraction analysis. Addition of pyridine and t-butyl pyridine to azide 2 afford the corresponding pyridine adducts. Compound la as well as the Lewis base adducts of 2 have been characterized by multinuclear NMR spectroscopy, and the structures were confirmed by X-ray diffraction analysis. The structural features of azide 2 and the strong Lewis acidity of its boron center have also been investigated by computational chemistry techniques at the MP2 level of theory.

  DOI：

  10.1021/ic902436s
• 作为产物：
  描述：

  biphenyl-2,2'-diyl-bis-lithium 以 正己烷 、 二氯甲烷 为溶剂， 生成 9-azido-9-borafluorene
  参考文献：
  名称：

  Synthesis and Structural Characterization of 9-Azido-9-Borafluorene: Monomer and Cyclotrimer of a Borole Azide

  摘要：

  The reaction of 2,2'-dilithiobiphenyl, generated from 2,2'-dibromobiphenyl and n-BuLi, with BCl3 using n-hexane as solvent provides a high-yielding, simple preparative route to 9-chloro-9-borafluorene la. This in turn can be reacted with trimethylsilyl azide to yield 9-azido-9-borafluorene 2. Compound 2 exists as a cyclic trimer in the solid state, but in dichloromethane solution the monomer can coexist with the trimer. Azide 2 is rather unstable both in the solid state and in solution, and it transforms with trace amounts of water and oxygen to the 1,3,5-tris(2-biphenylyl)cyclotriboroxane that was characterized by X-ray diffraction analysis. Addition of pyridine and t-butyl pyridine to azide 2 afford the corresponding pyridine adducts. Compound la as well as the Lewis base adducts of 2 have been characterized by multinuclear NMR spectroscopy, and the structures were confirmed by X-ray diffraction analysis. The structural features of azide 2 and the strong Lewis acidity of its boron center have also been investigated by computational chemistry techniques at the MP2 level of theory.

  DOI：

  10.1021/ic902436s