1,2-(2,5-cyclohexadiene-1,4-diyl)-ortho-carborane | 183127-42-6

• 英文名称: 1,2-(2,5-cyclohexadiene-1,4-diyl)-ortho-carborane
• CAS: 183127-42-6
• 化学式: C₈H₁₆B₁₀
• 分子量: 220.325
• InChiKey: QKXNQGMRYANVAK-OLQVQODUSA-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：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  1-iodo-2-lithio-1,2-carborane 、 苯 以 benzene 为溶剂， 以25%的产率得到1,2-(2,5-cyclohexadiene-1,4-diyl)-ortho-carborane
  参考文献：
  名称：

  Insertion of Carboryne into Aromatic Rings: Formation of Cyclooctatetraenocarboranes

  摘要：

  1-lodo-2-lithiocarborane is an efficient precursor to carboryne. It can react with arenes to give different types of dearomatization products, [4+2] cycloaddition and/or cycloinsertion products, dependent upon the substituents on the aromatic rings. The formal cycloinsertion products, cyclooctatetraenocarboranes, is generated from the [2+2] cycloaddition intermediates followed by thermal [3,3] sigmatropic rearrangement. This novel dearomatization of arenes with carboryne also serves as an important method for the synthesis of cyclooctatetraenocarboranes.

  DOI：

  10.1021/ja1044488

文献信息

• Nickel-Catalyzed Regioselective [2+2+2] Cycloaddition of Carboryne with Alkynes
  作者：Zaozao Qiu、Sunewang R. Wang、Zuowei Xie

  DOI：10.1002/anie.201001249

  日期：2010.6.21

  A View [2+2+2] a Kill: For the first time, nickel‐catalyzed [2+2+2] cycloaddition reactions of alkynes or diynes with carboryne using 1‐iodo‐2‐lithiocarborane as a precursor have been achieved. The mechanism is proposed after the structural confirmation of the key intermediate, nickelacyclopentene.

  视图[2 + 2 + 2]必杀技：首次实现了以1-碘-2--2-硫代碳硼烷为前驱体的镍催化炔或二炔与碳炔的[2 + 2 + 2]环加成反应。在关键中间体镍环戊烯的结构确认后提出了该机理。