| 1236277-49-8

• CAS: 1236277-49-8
• 化学式: C₉H₁₈B₁₀
• 分子量: 234.352
• InChiKey: ZDORTLPBRNPMAA-KNVOCYPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 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 、 甲苯 以 toluene 为溶剂， 生成 、
  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

• Reaction of Carboryne with Alkylbenzenes
  作者：Sunewang Rixin Wang、Zuowei Xie

  DOI：10.1021/om300129t

  日期：2012.4.23

  Carboryne (1,2-dehydro-o-carborane), in situ generated from the precursor 1-iodo-2-lithiocarborane, reacted with alkylbenzenes to give two regioisomers of the [4 + 2] cycloadducts as the major products in moderate to good yields, in which the steric factors play an important role in the regioselectivity. Minor products derived from benzylic C–H insertion reaction, annulation reaction, tandem [4 + 2]

  由前体1-碘-2-硫代碳烷原位生成的碳硼烷（1,2-脱氢-邻-甲硼烷）与烷基苯反应生成[4 + 2]环加合物的两种区域异构体，为中等至良好的主要产物产生，其中空间因素在区域选择性中起重要作用。还分离了衍生自苄基CH插入反应，环化反应，串联[4 + 2]环加成/同位Diels-Alder反应和串联烯反应/ [2 + 2]环加成的次要产物，并将其表征为碳炔与甲苯。在上述反应中AgF的存在没有引起产物分布和产率的显着变化。