9-azido-9-borafluorene*(tert-butyl pyridine)

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 9-azido-9-borafluorene*(tert-butyl pyridine)
• 英文别名: 9-azido-9-borafluorene*t-butyl-pyridine；1-(8-Azido-8-boranuidatricyclo[7.4.0.02,7]trideca-1(13),2,4,6,9,11-hexaen-8-yl)-4-tert-butylpyridin-1-ium；1-(8-azido-8-boranuidatricyclo[7.4.0.02,7]trideca-1(13),2,4,6,9,11-hexaen-8-yl)-4-tert-butylpyridin-1-ium
• 化学式: C₂₁H₂₁BN₄
• 分子量: 340.236
• InChiKey: AUWOSCGRJJEEKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  18.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 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*(tert-butyl pyridine)
  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

文献信息

• Synthesis and Structural Characterization of 9-Azido-9-Borafluorene: Monomer and Cyclotrimer of a Borole Azide
  作者：Sunanda Biswas、Iris M. Oppel、Holger F. Bettinger

  DOI：10.1021/ic902436s

  日期：2010.5.17

  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.