N-benzyl-N-(diphenylmethylene)-1,1,1-tris(perfluorophenyl)-l4-boranaminium | 418759-04-3

• 英文名称: N-benzyl-N-(diphenylmethylene)-1,1,1-tris(perfluorophenyl)-l4-boranaminium
• CAS: 418759-04-3
• 化学式: C₃₈H₁₇BF₁₅N
• 分子量: 783.347
• InChiKey: QDAJEJQMFBMSOB-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：

  N-(二苯基亚甲基)-1-苯甲胺 、 三(五氟苯基)硼烷 以 甲苯 为溶剂， 以90%的产率得到N-benzyl-N-(diphenylmethylene)-1,1,1-tris(perfluorophenyl)-l4-boranaminium
  参考文献：
  名称：

  Solution and Solid-State Characteristics of Imine Adducts with Tris(pentafluorophenyl)borane

  摘要：

  Adducts of the N-benzyl imines Ph(R)C NBn (R = Ph, CH3, H) and Bu-t(CH3)C=NBn and the N-phenyl imine Ph(H)C=NPh with the Lewis acid tris(pentafluorophenyl)borane, B(C6F5)(3), have been prepared and characterized in solution and in the solid state. For each imine, the Lewis acid is N-bound, with the exception of the sterically demanding base Bu-t(CH3)C NBn, which reacts with B(C6F5)(3) through its enamine tautomer to form an alpha-C bound adduct, 5. In the N-bound imine-borane adducts 1-4, steric crowding and pi-stacking between C6F5 and C6H5 rings results in restricted rotation about the B-N and B-C bonds; the dynamic behavior which results can be studied using variable-temperature F-19 and H-1 NMR spectroscopy. For the unsymmetrical ketimines and aldimines, kinetic adducts of the thermodynamically dominant free imine are observed to form initially upon treatment with B(C6F5)(3); these adducts slowly convert thermally to the thermodynamic adducts of the less stable imine. For the ketimine Ph(CH3)C=NBn, both the kinetic adduct 2-k and the thermodynamic adduct 2-t were fully characterized. In the solid-state structures of all the adducts except 5, one or two C6F5/C6H5 stacking interactions are present; in one case, the adduct 3-t between B(C6F5)(3) and Ph(H)C=NBn, intermolecular stacking interactions are apparent in the crystal-packing diagram. The implications of the structures of these adducts for Lewis acid mediated addition of nucleophiles to imines is discussed.

  DOI：

  10.1021/om011086n