tetrahydrofuran*(chloro)dihydroborane | 856612-25-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tetrahydrofuran*(chloro)dihydroborane
• 英文别名: tetrahydro-furan; compound with chloroborane；Tetrahydro-furan; Verbindung mit Chlorboran；chloroborane;oxolane
• CAS: 856612-25-4
• 化学式: BClH₂*C₄H₈O
• 分子量: 120.387
• InChiKey: GLHXHWUDOMEPFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.57
• 重原子数：
  7.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  dinitramide potassium salt 、 tetrahydrofuran*(chloro)dihydroborane 以 四氢呋喃 为溶剂， 反应 4.0h， 以41%的产率得到
  参考文献：
  名称：

  N，N-二硝基氨基硼烷配合物的合成与结构

  摘要：

  硼烷轰隆！用N，N-二硝基酰胺盐将卤化物取代在卤硼烷或二溴硼烷配合物中，可以提供多种N，N-二硝基氨基硼烷配合物，收率高且分析纯净（参见方案; Alk =烷基，py =吡啶，THF =四氢呋喃）。

  DOI：

  10.1002/asia.201700603
• 作为产物：
  描述：

  tetraoctadecylammonium chloride 、 borane tetrahydrofuran 在 catalyst:Rhcolloid/[Oct₄N]Cl 作用下， 以 四氢呋喃 为溶剂， 生成 tetrahydrofuran*(chloro)dihydroborane
  参考文献：
  名称：

  Poisoning of Heterogeneous, Late Transition Metal Dehydrocoupling Catalysts by Boranes and Other Group 13 Hydrides

  摘要：

  Borane reagents are widely used as reductants for the generation of colloidal metals. When treated with a variety of heterogeneous catalysts such as colloidal Rh, Rh/Al2O3, and Rh(0) black, BH3 center dot THF (THF = tetrahydrofuran) was found to generate H-2 gas with the concomitant formation of a passivating boron layer on the surface of the Rh metal, thereby acting as a poison and rendering the catalyst inactive toward the dehydrocoupling of Me2NH center dot BH3. Analogous poisoning effects were also detected for (i) colloidal Rh treated with other species containing B-H bonds such as [HB-NH](3), or Ga-H bonds such as those present in GaH3 center dot OEt2, (ii) colloidal Rh that was generated from Rh(I) and Rh(III) salts using borane or borohydrides as reductants, and (iii) for other metals such as Ru and Pd. In contrast, analogous poisoning effects were not detected for the catalytic hydrogenation of cyclohexene using Rh/Al2O3 or the Pd-catalyzed Suzuki cross-coupling of PhB(OH)(2) and PhI. These results suggest that although this poisoning behavior is not a universal phenomenon, the observation that such boron layers are formed and surface passivation may exist needs to be carefully considered when borane reagents are used for the generation of metal colloids for catalytic or materials science applications.

  DOI：

  10.1021/ja0447412

文献信息

• In Situ preparation of mono- and dichloroboranes and their reactivity with olefins
  作者：George Zweifel

  DOI：10.1016/s0022-328x(00)83723-7

  日期：1967.8

  hydrogen to form monochloroborane. Dichloroborane is obtained when two moles of hydrogen chloride are reacted with one mole of borane. Hydroboration of 1-hexene with these reagents involves an anti-Markownikoff addition of the B-H bond to the olefin. Chloroboranes exhibit a markedly lower reactivity toward olefins as compared with borane or alkylboranes. The reaction of olefins with monochloroborane in a 1

  用氯化氢以1：1的比例处理四氢呋喃中的硼烷（BH 3），导致立即释放出一摩尔氢形成一氯硼烷。当两摩尔的氯化氢与一摩尔的硼烷反应时，得到二氯硼烷。用这些试剂对1-己烯进行氢硼化涉及将BH键抗Markowniknikoff加到烯烃上。与硼烷或烷基硼烷相比，氯硼烷显示出对烯烃的显着较低的反应性。烯烃与一氯硼烷以1：1的比例反应，优先生成单烷基氯硼烷。因此，用该试剂对1-己烯进行氢硼化，然后将中间体有机硼烷水解，得到67％的正己基硼酸。
• The reaction of diborane with boron trichloride in the presence of ethers—The chloroborane etherates
  作者：Herbert C. Brown、P.A. Tierney

  DOI：10.1016/0022-1902(59)80010-5

  日期：1959.1

  Diborane does not react to any significant extent with boron trichloride in the absence of ethers. In the presence of ethers (dimethyl ether, diethyl ether, diglyme, tetrahydrofuran and tetrahydropyran) reaction readily occurs at room temperatures to form chloroborane etherates, as indicated by the equations: B2H6 + BCl3 + 3R2O → 3H2ClB·OR2B2H6 + 4BCl3 + 6R2O → 6HCl2B·OR2 These chloroborane etherates

  在不存在醚的情况下，乙硼烷不会与三氯化硼发生任何显着反应。在醚（二甲醚，二乙醚，二甘醇二甲醚，四氢呋喃和四氢吡喃）的存在下，在室温下容易发生反应，形成氯硼烷醚化物，如方程式所示：B 2 H 6 + BCl 3 + 3R 2 O→3H 2 ClB ·OR 2 B 2 H 6 + 4BCl 3 + 6R 2 O→6HCl 2 B·OR 2这些氯硼烷醚化物也可以根据以下反应由碱金属硼氢化物合成：MBH 4 + BCl3 + 2R 2 O→：2H 2 ClB·OR 2 + NaClMBH 4 + 3BCl 3 + 4R 2 O→：4HCl 2 B·OR 2 + NaCl它们的形成解释了乙硼烷处理碱金属硼氢化物时乙硼烷收率低。乙醚溶液中过量的三氯化硼。已经分离和表征了许多氯硼烷醚化物。它们与烯烃反应形成有机硼烷衍生物，并还原典型酮中的羰基，但不还原酯中的羰基。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.9, 6.2.5, page 292 - 302
  作者：

  DOI：——

  日期：——
• Transfer Reactions Involving Boron. XI. The Reaction of Monochloro- and Dichloroborane with Olefins
  作者：Daniel J. Pasto、Padma. Balasubramaniyan

  DOI：10.1021/ja00978a023

  日期：1967.1
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.9, 1.4.3.1, page 40 - 41
  作者：

  DOI：——

  日期：——