(2,6-Mes2C6H3BH2)2 | 488838-60-4

• 英文名称: (2,6-Mes2C6H3BH2)2
• 英文别名: [2,6-Mes2C6H3BH(μ-H)]2
• CAS: 488838-60-4
• 化学式: C₄₈H₅₄B₂
• 分子量: 652.579
• InChiKey: OXXNXOYMYHHPQU-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

• 作为产物：
  描述：

  [2,6-Mes2C6H3Li]2 、 chloroborane*dimethylsulfide 以 乙醚 为溶剂， 以54%的产率得到(2,6-Mes2C6H3BH2)2
  参考文献：
  名称：

  Unsymmetrical 9-Borafluorenes via Low-Temperature C−H Activation of m-Terphenylboranes

  摘要：

  The reaction of 2,6-(4-t-BuC6H4)(2)C6H3Li and with H2ClB.SMe2 or HCl2B.SMe2 in hexane solution afforded the m-terphenyl-substituted unsymmetrical 9-borafluorene 1-(4-tertbutylphenyl)-7-tert-butyl-9-(bis-2,6-(4-tert-butylphenyl)phenyl)-9-borafluorene, 1, in good to moderate yields. The related reaction of 2,6-(3,5-Me2C6H3)(2)C6H3Li with BH2Cl.SMe2 or BHCl2.SMe2 in toluene solution gave 1-(3,5-dimethylphenyl)-6,8-dimethyl-9-(bis-2,6-(3,5-dimethylphenyl)phenyl)-9-borafluorene, 3. Compounds 1 and 3 are air-stable fluorescent solids. The reactions of 2,6-(2-MeC6H4)(2)C6H3Li or 2,6-Mes(2)C(6)H(3)Li (which possess either two or no o- and o"-hydrogens) with H2ClB.SMe2 gave the primary boranes [2,6-(2-MeC6H4)(2)C6H3BH2](2), 4, and [2,6-Mes(2)C(6)H(3)BH(2)](2), 5, respectively. Quenching of the reaction of 2,6-(4-tBuC(6)H(4))(2)C6H3Li with H2ClB.SMe2 after 1.5 h with pyridine resulted in the isolation of the primary borane [2,6-(4-t-BuC6H4)(2)C6H3BH2](2), 2, as the pyridine adduct 2.py, which after thermolysis at 190 degreesC gave 1-(4-tert-butylphenyl)-7-tert-butyl-9-borafluorene-pyridine, 7.py. Heating a C6D6 solution of 4 to 60-70 degreesC led to C-H activation and formation of a 1:1 adduct of monomeric 4 and 1-(2-methylphenyl)-5-methyl-9-borafluorene, 12. Reaction of 2 equiv of 2,6-(4-t-BuC6H4)(2)C6H3Li with H2ClB.SMe2 in hexane solution followed by addition of THF gave the very crowded diterphenyl borate [2,6-(4-t-BuC6H4)(2)C6H3](2)B(mu-H)(2)Li(THF)(2)](2), 11, which can be converted to I by simple addition of water. Prolonged exposure of I to concentrated aqueous HCl led to B-C bond cleavage and formation of the sterically very crowded diterphenylborinic acid [2,6-(4-t-BuC6H4)(2)C6H3](2)BOH, 15. All compounds have been characterized by H-1, C-13, and B-11 NMR spectroscopy and mass spectrometry, and compounds 1, 4, and 11 have also been characterized by single-crystal X-ray crystallography.

  DOI：

  10.1021/om020611v

文献信息

• Synthesis and Characterization of a Sterically Encumbered Unsymmetrical 9-Borafluorene, Its Pyridine Adduct, and Its Dilithium Salt
  作者：Rudolf J. Wehmschulte、Masood A. Khan、Brendan Twamley、Berthold Schiemenz

  DOI：10.1021/om000868y

  日期：2001.3.1

  The reaction of 2,6-(4-t-BuC6H4)(2)C6H3Li with BH2Cl . SMe2 in hexane or Et2O solution affords the terphenyl-substituted unsymmetrical 9-borafluorene 1-(4-tert-butylphenyl)-7-tertbutyl-9-(bis-2,6-(4-tert-butylphenyl)phenyl)-9-borafluorene (1) in good to moderate yields. Addition of pyridine gives the colorless crystalline adduct 1.py. Compound 1 is readily reduced to the deep red heteroaromatic dianionic (mu (2)-eta (5),eta (5)-1-(4-tert-butylphenyl)-7-tert-butyl-9-(bis-2,6-(4-tert-butylphenyl)phenyl)-9-borafluorenyl)bis(diethyl ether)dilithium (2) with excess lithium powder in Et2O solution. Reactions of the dianionic 2 with various metal salts leads to reduction of these salts, and bright yellow 1 is recovered in essentially quantitative yields. Compounds 1, 1.py, and 2 were characterized by H-1,C-13, and B-11 NMR spectroscopy and compounds 1.py and 2 also by single-crystal X-ray diffraction.