| 203304-08-9

• CAS: 203304-08-9
• 化学式: C₂₆H₈BF₁₅O
• 分子量: 632.136
• InChiKey: FAWOOSLYMWVHQO-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：

  、 苯甲醛 以 氘代苯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Solution and Solid-State Structures of Tris(pentafluorophenyl)borane Adducts of PhC(O)X (X = H, Me, OEt, NPrⁱ₂)

  摘要：

  Reaction of the highly electrophilic borane B(C6F5)(3) with the carbonyl Lewis bases benzaldehyde,acetophenone, ethyl benzoate, and N,N-diisopropylbenzamide led to isolation of the crystalline adducts 1-H, 1-Me, 1-OEt, and 1-NPr, respectively, in good to excellent yields(63-89%). Equilibrium measurements and exchange experiments indicated that the order of basicity (from highest to lowest) of these bases toward B(C6F5)(3) follows the order N,N-diisopropylbenzamide > benzaldehyde > acetophenone > ethylbenzoate. The solution and solid-state structures were probed to rationalize these observations. In solution, the borane coordinates to the carbonyl lone pair syn to H and Me in the aldehyde and ketone adducts, as indicated by H-1/F-19 NOE difference experiments. The same coordination geometry was observed in the solid state upon X-ray diffraction analysis of the two adducts. The added front strain associated with the ketone adduct (C-O-B = 133.6(3)degrees vs 126.7(5)degrees for the benzaldehyde complex) accounts for the observed order of basicity with these two bases. For ethyl benzoate and N,N-diisopropylbenzamide, the borane coordinates syn to the phenyl group in both solution and the solid state. In addition to the carbonyl oxygen-boron interaction, the two complexes engage in a pi-stacking interaction between one of the borane C6F5 rings and the syn phenyl group. In addition to the structural proof of this interaction in the solid state, variable-temperature F-19 NMR experiments suggest it is important in the solution structures of these adducts as well.

  DOI：

  10.1021/om9710327
• 作为产物：
  描述：

  以 氘代苯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Solution and Solid-State Structures of Tris(pentafluorophenyl)borane Adducts of PhC(O)X (X = H, Me, OEt, NPrⁱ₂)

  摘要：

  Reaction of the highly electrophilic borane B(C6F5)(3) with the carbonyl Lewis bases benzaldehyde,acetophenone, ethyl benzoate, and N,N-diisopropylbenzamide led to isolation of the crystalline adducts 1-H, 1-Me, 1-OEt, and 1-NPr, respectively, in good to excellent yields(63-89%). Equilibrium measurements and exchange experiments indicated that the order of basicity (from highest to lowest) of these bases toward B(C6F5)(3) follows the order N,N-diisopropylbenzamide > benzaldehyde > acetophenone > ethylbenzoate. The solution and solid-state structures were probed to rationalize these observations. In solution, the borane coordinates to the carbonyl lone pair syn to H and Me in the aldehyde and ketone adducts, as indicated by H-1/F-19 NOE difference experiments. The same coordination geometry was observed in the solid state upon X-ray diffraction analysis of the two adducts. The added front strain associated with the ketone adduct (C-O-B = 133.6(3)degrees vs 126.7(5)degrees for the benzaldehyde complex) accounts for the observed order of basicity with these two bases. For ethyl benzoate and N,N-diisopropylbenzamide, the borane coordinates syn to the phenyl group in both solution and the solid state. In addition to the carbonyl oxygen-boron interaction, the two complexes engage in a pi-stacking interaction between one of the borane C6F5 rings and the syn phenyl group. In addition to the structural proof of this interaction in the solid state, variable-temperature F-19 NMR experiments suggest it is important in the solution structures of these adducts as well.

  DOI：

  10.1021/om9710327