1-(thiophen-2-yl)-1,2-dicarba-closo-dodecaborane | 171816-44-7

• 英文名称: 1-(thiophen-2-yl)-1,2-dicarba-closo-dodecaborane
• 英文别名: thiophene-2-yl-o-carborane
• CAS: 171816-44-7
• 化学式: C₆H₁₄B₁₀S
• 分子量: 226.353
• InChiKey: OOXIYLUMUFFOCL-UHFFFAOYSA-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

• 作为反应物：
  描述：

  1-(thiophen-2-yl)-1,2-dicarba-closo-dodecaborane 在 溴 、 碳酸氢钠 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以58%的产率得到
  参考文献：
  名称：

  Electronic Alteration on Oligothiophenes by o-Carborane: Electron Acceptor Character of o-Carborane in Oligothiophene Frameworks with Dicyano-Vinyl End-On Group

  摘要：

  We studied electronic change in oligothiophenes by employing o-carborane into a molecular array in which one or both end(s) were substituted by electron-withdrawing dicyano-vinyl group(s). Depending on mono- or bis-substitution at the o-carborane, a series of linear A(1)-D-A(2) (1a-1c) or V-shaped A(1)-D-A(2)-D-A(1) (2a-2c) oligothiophene chain structures of variable length were prepared; A(1), D, and A(2), represent dicyano-vinyl, oligothiophenyl, and o-carboranyl groups, respectively. Among this series, 2a shows strong electron-acceptor capability of o-carborane comparable to that of the dicyano-vinyl substituent, which can be elaborated by a conformational effect driven by cage sigma-*-pi* interaction. As a result, electronic communications between o-carborane and dicyano-vinyl groups are successfully achieved in 2a.

  DOI：

  10.1021/acs.joc.5b00336
• 作为产物：
  描述：

  2-碘噻吩 、 1,2-dicarba-closo-dodecaborane(12) 在 copper(l) iodide 、 silver carbonate 、 lithium tert-butoxide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.0h， 以15%的产率得到1-(thiophen-2-yl)-1,2-dicarba-closo-dodecaborane
  参考文献：
  名称：

  光促进铜催化的邻碳烷的笼状C-芳基化反应：轻松合成1-芳基-邻碳烷和邻碳烷稠合的环

  摘要：

  已经实现了光促进的，铜催化的邻氨基甲酸酯与芳基卤化物的笼型CH–H芳基化反应，从而轻松合成了各种1-芳基邻氨基甲酸酯和邻氨基甲烷稠合的环状物。该方法具有以下特点：（1）使用邻氨基甲酸酯代替预官能化的碘代氨基甲酸酯作为起始原料；（2）采用富土铜作为催化剂；（3）室温反应。对照实验表明该反应通过Cu催化的自由基偶联进行。

  DOI：

  10.1039/d0nj02029j

文献信息

• Synthesis, structure and physical properties of tetrathiafulvalenium salts of the ferracarborane complex commo-[3,3′-Fe{1-(C₄H₃S)-1,2-C₂B₉H₁₀}₂]^–
  作者：Yaw-Kai Yan、D. Michael P. Mingos、Mohamedally Kurmoo、Wan-Sheung Li、Ian J. Scowen、Mary McPartlin、A. Treeve Coomber、Richard H. Friend

  DOI：10.1039/dt9950002851

  日期：——

  The sandwich complex commo-[3,3'-fe1-(C(4)H(3)S)-1.2-C(2)B(9)H(10)}(2)](-)1 and its tetrathiafulvalenium salts [ttf](5)[Fe(C(2)B(9)H(10)C(4)H(3)S)(2)] 2 and [ttf] [Fe(C(2)B(9)H(10)C(4)H(3)S)(2)] 3 were synthesised in order to study the effect of the thiophene:(C(4)H(3)S) group on the crystal packing, electrical and magnetic properties of ttf-metallacarborane salts. The crystal structure of 2 features unusual two-dimensional networks of ttf units which extend in the a and c directions. Each ttf sheet contains stacked trimers of ttf units, which propagate along the a direction, and bridging ttf units, which lie between the ttf stacks approximately orthogonally to the ttf units within the trimers. The trimers are linked along the c direction via short S ... S contacts (3.56 Angstrom) with these bridging ttf units. In contrast, the crystal structure of compound 3 contains discrete stacked dimers of [ttf](.+) cations. Whilst crystals of 2 are semiconducting (sigma(300K) = 2 x 10(-3) S cm(-1)) with an activation;energy of 0.22 eV, those of 3 are insulating (sigma(290K) less than or equal to 10(-7) S cm(-1)). Both compounds exhibit weak ferromagnetic interactions between the unpaired spins of their [Fe(C(2)B(9)H(10)C(4)H(3)S)(2)](-) anions, with small positive Weiss constants of 1.9 and 0.5 K respectively.