9-iodo-o-carborane | 17830-03-4

• 英文名称: 9-iodo-o-carborane
• 英文别名: 9-iodo-1,7-dicarba-closo-dodecaborane(12)；9-iodo-1,2-dicarba-closo-dodecaborane；9-iodo-1,2-dicarbadodecaborane；9-iodo-1,2-dicarbaundecaborate；9-iodo-closo-o-carborane；9-iodo-1,2-carborane
• CAS: 17830-03-4
• 化学式: C₂H₁₁B₁₀I
• 分子量: 270.124
• InChiKey: JUYNIFRVBCJZRY-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：

  9-iodo-o-carborane 在 三氯化铝 碘 、 sodium thiosulfate 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 以80.3%的产率得到9,12-diiodo-1,2-dicarba-closo-dodecarborane(12)
  参考文献：
  名称：

  Li, Ji; Logan, Cameron F.; Jones Jr., Maitland, Inorganic Chemistry, 1991, vol. 30, # 25, p. 4866 - 4868

  摘要：

  DOI：
• 作为产物：
  描述：

  (η2-9-I-1,2-C2B10H9)Ni(PPh3)2*0.5(toluene) 以 四氢呋喃 为溶剂， 生成 9-iodo-o-carborane
  参考文献：
  名称：

  Synthesis and Structural Characterization of Group 10 Metal−Carboryne Complexes

  摘要：

  A series of group 10 metal-carboryne complexes were prepared from an equimolar reaction of MCl2(PR3)(2) with Li2C2B10H10-nXn (M = Ni, Pd, Pt; X = Br, I, Ph; n = 0, I, 2). They were fully characterized by various spectroscopic techniques, elemental analyses, and X-ray diffraction studies. These complexes have similar solid-state structures, in which the metal atom is bonded to two cage carbon atoms and coordinated to two phosphorus atoms in a planar geometry. The coordinated phosphines are labile and can be replaced by other Lewis bases. The bonding interactions between the metal and the carboryne unit can be described as a resonance hybrid of both the M-C sigma- and M C pi-bonding forms. These complexes can be viewed as 16e species.

  DOI：

  10.1021/om100669x

文献信息

• Catalytic Oxidative Dehydrogenative Coupling of Cage B–H/B–H Bonds for Synthesis of Bis(<i>o</i>-carborane)s
  作者：Ji Wu、Ke Cao、Cai-Yan Zhang、Tao-Tao Xu、Li-Fang Ding、Bo Li、Junxiao Yang

  DOI：10.1021/acs.orglett.9b02129

  日期：2019.8.2

  protocol for synthesis of bis(o-carborane) connected by a B–B bond via palladium catalyzed oxidative dehydrogenative coupling of cage B–H/B–H bonds was developed for the first time. A series of bis(o-carborane)s connected by B(4)–B(4)′ and B(4)–B(5)′ bonds was synthesized with moderate to good yields. This work opens the door for miscellaneous applications of bis(o-carborane) in related disciplines

  首次开发了一种高效，简洁的方案，用于合成通过笼罩式BH / BH键的钯催化氧化脱氢偶联而通过BB键连接的双（邻-甲硼烷）。合成了一系列通过B（4）–B（4）'和B（4）–B（5）'键连接的双（邻-甲碳烷），收率中等至良好。这项工作为双（邻-碳硼烷）在相关学科中的其他应用打开了大门，并且在设计和合成不同种类的双碳硼烷中具有重要的价值。
• Mercuration ofB(9)-substitutedmeta- andortho-carboranes
  作者：A. Ya. Usyatinsky、K. V. Budkina、P. V. Petrovskii、V. I. Bregadze

  DOI：10.1007/bf00698511

  日期：1995.4

  The mercuration of substituted R2C2B10H9X-9 type carboranes (where R=m-H, X= Cl, Br, I, Me; R=o-H, X=Me) was studied. It was found that mercury atoms add to the boron atoms in position 10 ofmeta-carboranes and in position 12 ofortho-carboranes,i.e., to the boron atoms adjacent to the boron atom bonded to the X substituent. Symmetrical (R2C2B10H8X)2Hg type derivatives were obtained. It was shown that

  研究了取代的 R2C2B10H9X-9 型碳硼烷（其中 R=mH，X=Cl、Br、I、Me；R=oH，X=Me）的汞化。发现汞原子加到间碳硼烷的10位和邻位碳硼烷的12位的硼原子上，即加到与与X取代基键合的硼原子相邻的硼原子上。获得了对称的 (R2C2B10H8X)2Hg 型衍生物。结果表明，它们可用作金属转移反应的起始原料。
• A facile approach for the synthesis of <i>nido</i>-carborane fused oxazoles <i>via</i> one pot deboronation/cyclization of 9-amide-<i>o</i>-carboranes
  作者：Cai-Yan Zhang、Ke Cao、Tao-Tao Xu、Ji Wu、Linhai Jiang、Junxiao Yang

  DOI：10.1039/c8cc07728b

  日期：——

  A one pot deboronation/cyclization of 9-amide-o-carboranes for the synthesis of nido-7,8-carborane fused oxazole by cooperation of Pd(OAc)2, AgOAc and K2CO3 has been developed. A plausible mechanism involving an amide directed electrophilic palladation of the B–H bond and deboronation/cyclization process was proposed based on the successful isolation and structural characterization of the key deboronated

  9-酰胺的一锅脱硼/环化ø -carboranes用于合成巢加入Pd（OAC）的合作稠合恶唑硼烷-7,8- 2，AgOAc和K 2 CO 3已经研制成功。基于成功的关键脱硼中间体的分离和结构表征，提出了一种可能的机理，该机理涉及酰胺键的B-H键亲电性palpalation和脱硼/环化过程。
• Oxidative Generation of Boron-Centered Radicals in Carboranes
  作者：Harrison A. Mills、Joshua L. Martin、Arnold L. Rheingold、Alexander M. Spokoyny

  DOI：10.1021/jacs.0c00300

  日期：2020.3.11

  dichalcogenides, and N-heterocycles, yielding the corresponding substituted carboranes containing B-O, B-S, B-Se, B-Te, and B-C bonds. Remarkably, this chemistry tolerates various electronic environments, providing access to facile substitution chemistry at both electron-rich and electron-poor B-H vertices in carboranes.

  我们报告了第一次间接观察和使用由改性碳硼酰前体氧化产生的以硼顶点为中心的碳硼酰自由基。这些自由基中间体是通过硼簇笼和外多面体硼基取代基（例如-BF3K、-B(OH)2）之间的BB键的直接氧化形成的。原位生成的自由基物种被证明是与基于氧的自由基、二硫属化物和 N-杂环反应的有效底物，产生含有 BO、BS、B-Se、B-Te 和 BC 键的相应取代碳硼烷。值得注意的是，这种化学能耐受各种电子环境，在碳硼烷中的富电子和缺电子 BH 顶点处提供了简便的取代化学。
• New Approach to the Synthesis of 3-Alkyl-1,2-dicarba-<i>closo</i>-dodecaboranes: Reaction of Alkyldichloroboranes with Thallium Dicarbollide
  作者：Alexander V. Safronov、Natalia I. Shlyakhtina、M. Frederick Hawthorne

  DOI：10.1021/om201060e

  日期：2012.4.9

  2-dicarba-closo-dodecaboranes were prepared in good yields via the reaction of alkyldichloroboranes, which were generated in situ through hydroboration of the corresponding alkenes with a dichloroborane–dioxane complex, with thallium dicarbollides in anhydrous dichloromethane at room temperature. This reaction also affords insertion products with new thallium dicarbollides prepared from 3-iodo- and 9-iodo-1,2-dic

  许多3-烷基取代的1,2- dicarba-闭合碳-dodecaboranes经由alkyldichloroboranes的反应，其产生了良好的收率制备原位与通过相应的烯烃的硼氢化一个二氯硼二恶烷络合物，铊dicarbollides在室温下用无水二氯甲烷洗脱。该反应还得到插入产品具有新铊dicarbollides从3-碘和9-碘代-1,2- dicarba-制备闭合碳-dodecaboranes。将合成的3-烷基-1,2- dicarba-闭合碳-dodecaboranes可以在B（6）原子被选择性地脱硼，以形成阴离子的3-烷基-7,8- dicarba-巢-undecaborates。所有化合物均通过NMR和MS技术表征。