lithium [((N-2,6-diisopropylphenyl)formimidoyl)cyclopentadienide] | 329006-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: lithium [((N-2,6-diisopropylphenyl)formimidoyl)cyclopentadienide]
• 英文别名: lithium;1-cyclopenta-2,4-dien-1-yl-N-[2,6-di(propan-2-yl)phenyl]methanimine;oxolane
• CAS: 329006-45-3
• 化学式: C₃₀H₄₆LiNO₃
• 分子量: 475.641
• InChiKey: XCAFGDBXCKQSKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  lithium [((N-2,6-diisopropylphenyl)formimidoyl)cyclopentadienide] 、 iron(II) chloride 以 甲苯 为溶剂， 以79%的产率得到1,1'-bis[(N-2,6-diisopropylphenyl)formimidoyl]ferrocene
  参考文献：
  名称：

  Synthesis and Structural and Chemical Features of Formimidoyl-Functionalized Lithium Cyclopentadienides

  摘要：

  Treatment of 6-dimethylaminofulvene (1) with lithium anilide (2a) yields lithium [(N-phenylformimidoyl)cyclopentadienide], 3a, by an anilide addition/dimethylamine elimination reaction sequence. Similar treatment of 1 with the reagents Li[HNAr] [Ar = p-tolyl (2b), -2,6-dimethylphenyl (2c), or -2,6-diisopropylphenyl (2d)] gave the corresponding Li[C5H4 CH=NAr] products 3b, 3c, and 3d in good yields (80-90% isolated) as THF adducts. Crystallization from THF gave 3d.3THF, which was characterized by X-ray diffraction. It contains monomeric units in the solid state. The lithium atom is coordinated to the imino nitrogen atom and to three THF molecules in a tetrahedral arrangement. The C5H4 unit shows some residual bond alternation. In crystalline 3d it exhibits no contact to the alkali metal. The structural features of 3d can be described by a resonance hybrid of mesomeric structures of iminium-cyclopentadienide (i.e., C5H4CH=N(Li . 3THF)Ar, 3A) and of fulvenoide character (i.e., C5H4=CHN(Li . 3THF)Ar, 3B). The structure of 3c.3THF in the solid state is analogous. Complex 3a crystallizes with 1 equiv of THF. It exhibits a cyclodimeric structure (3a.THF)(2) in the crystal, where each Li atom is eta (5)-Cp- and N-K-coordinated to two different C5H4CH=NPh- ligands. The electrostatic nature of the Li-C and Li-N interactions results in very similar structural features of the C5H4CH=NAr- ligands in the complexes 3a, 3c, and 3d. The solution structures of these systems were characterized by temperature-dependent H-1 and Li-7 NMR spectra. The reagents 3a and 3d were employed in the synthesis of the respective bis [1, 1'-(N-aryl)formimidoyl] ferrocenes 4a and 4d (both isolated in ca. 80% yield). The complexes 4a and 4b were characterized by X-ray crystal structure analyses.

  DOI：

  10.1021/om000753u