9-azido-9-borafluorene | 1226990-06-2

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 9-azido-9-borafluorene
• 英文别名: 5-Azidobenzo[b][1]benzoborole；5-azidobenzo[b][1]benzoborole
• CAS: 1226990-06-2
• 化学式: C₁₂H₈BN₃
• 分子量: 205.027
• InChiKey: YRGVAMDEGMJDMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-azido-9-borafluorene 以 苯 为溶剂， 以92%的产率得到1.2,3.4,5.6-Tris-biphenylylen-(2,2')-borazin
  参考文献：
  名称：

  二苯并[c,e][1,2]氮杂硼啉的溶液相反应性：通过 BN-Aryne 活化并插入 Si-E 单键 (E=H, OSi(CH3)3, F, Cl)

  摘要：

  Si - F 键激活：BN-芳炔的 BN 三键具有极高的反应性，甚至可以激活惰性 Si−F 键以插入溶液中。该机制涉及硼和氟原子之间的配位相互作用，随后氮原子对硅进行亲核攻击。

  DOI：

  10.1002/chem.202103614
• 作为产物：
  描述：

  2,2'-双溴双苯 在 正丁基锂 、 叠氮基三甲基硅烷 作用下， 以 正己烷 、 正庚烷 为溶剂， 反应 73.33h， 生成 9-azido-9-borafluorene
  参考文献：
  名称：

  BN-菲：1,2-氮杂硼烷衍生物的环四聚

  摘要：

  9-叠氮基-9-硼芴在庚烷溶液中的热解产生BN-菲的四聚体。自陷产物的分离为BN-芳烃参与热解反应提供了证据。其形成可通过叠氮化物的脱氮和环扩大来​​合理化。

  DOI：

  10.1002/anie.201403213

文献信息

• <i>N</i>-Borane-Substituted Cyclic Phosphine Imides (BCPIs)
  作者：Shun Nagai、Takaya Hinogami、Sensuke Ogoshi、Yoichi Hoshimoto

  DOI：10.1246/bcsj.20230228

  日期：2023.12.15

  Bulletin of the Chemical Society of Japan, Ahead of Print.

  日本化学会会刊，印刷前。
• 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.
• BN-Phenanthryne: Cyclotetramerization of an 1,2-Azaborine Derivative
  作者：Matthias Müller、Cäcilia Maichle-Mössmer、Holger F. Bettinger

  DOI：10.1002/anie.201403213

  日期：2014.8.25

  Thermolysis of 9‐azido‐9‐borafluorene in heptane solution produces the tetramer of a BN‐phenanthryne. The isolation of the self‐trapping product provides evidence for the involvement of the BN‐aryne in the thermolysis reaction. Its formation may be rationalized by denitrogenation of the azide and ring enlargement.

  9-叠氮基-9-硼芴在庚烷溶液中的热解产生BN-菲的四聚体。自陷产物的分离为BN-芳烃参与热解反应提供了证据。其形成可通过叠氮化物的脱氮和环扩大来​​合理化。
• Solution Phase Reactivity of Dibenzo[c,e][1,2]azaborinine: Activation and Insertion into Si‐E Single Bonds (E=H, OSi(CH ₃ ) ₃ , F, Cl) by a BN‐Aryne
  作者：Constanze Keck、Jennifer Hahn、Divanshu Gupta、Holger F. Bettinger

  DOI：10.1002/chem.202103614

  日期：2022.1.24

  Si-F Bond Activation: The BN triple bond of a BN-aryne is extremely reactive and can even activate the inert Si−F bond for insertion in solution. The mechanism involves coordinative interaction between the boron and fluorine atoms followed by nucleophilic attack of the nitrogen atom on silicon.

  Si - F 键激活：BN-芳炔的 BN 三键具有极高的反应性，甚至可以激活惰性 Si−F 键以插入溶液中。该机制涉及硼和氟原子之间的配位相互作用，随后氮原子对硅进行亲核攻击。