N-(triphenylmethyl)(fluorodimesitylgermyl)phenylketenimine | 204134-67-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-(triphenylmethyl)(fluorodimesitylgermyl)phenylketenimine
• CAS: 204134-67-8
• 化学式: C₄₅H₄₂FGeN
• 分子量: 688.424
• InChiKey: OAKGHJVLMWPZDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.85
• 重原子数：
  48
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(triphenylmethyl)(fluorodimesitylgermyl)phenylketenimine 在 t-BuLi 作用下， 以 乙醚 、 氯仿 、 正戊烷 为溶剂， 生成 3,7-diphenyl-2,2,6,6-tetrakis(2,4,6-trimethylphenyl)-2,6-digerma-1,5-diazacyclooctatetra-3,4,7,8-ene
  参考文献：
  名称：

  An Eight-Membered Cyclic C,N-Bis(germadiyl) Bis(ketenimine)

  摘要：

  The reaction of tert-butyllithium with (fluorodimesitylgermyl)- and (chlorodimesitylgermyl)phenylacetonitrile (4a,b) leads to the lithium salts 5a (X = F) and 5b (X = Cl), which exhibit an ambident character: [> C--C=N <----> > C=C=N-]Li+. Quenching of 5a with triphenylbromomethane affords the germylketenimine 8, Mes(2)FGeC(Ph)=C=NCPh3. H-1 dynamic NMR spectroscopy allows the determination of the activation energy of the nitrogen inversion Delta G* = 9.9 +/- 0.2 kcal/mol. In the absence of a trapping reagent, 5 undergoes an elimination of lithium halide with formation of the eight-membered cyclic C,N-bis(germadiyl) bis(ketenimine) 1, which is the first ring containing two ketenimine moieties. 1 has been characterized by IR (nu(C=C=N) 2015 cm(-1)) and C-13 NMR spectroscopy (170.87 ppm for the sp carbon) and by an X-ray structure determination, which displays a "cyclohexane" type structure in a chair conformation.

  DOI：

  10.1021/om971014p
• 作为产物：
  描述：

  (fluorodimesitylgermyl)phenylacetonitrile 、 三苯基甲基溴 在 t-BuLi 作用下， 以 乙醚 、 正戊烷 为溶剂， 生成 N-(triphenylmethyl)(fluorodimesitylgermyl)phenylketenimine
  参考文献：
  名称：

  An Eight-Membered Cyclic C,N-Bis(germadiyl) Bis(ketenimine)

  摘要：

  The reaction of tert-butyllithium with (fluorodimesitylgermyl)- and (chlorodimesitylgermyl)phenylacetonitrile (4a,b) leads to the lithium salts 5a (X = F) and 5b (X = Cl), which exhibit an ambident character: [> C--C=N <----> > C=C=N-]Li+. Quenching of 5a with triphenylbromomethane affords the germylketenimine 8, Mes(2)FGeC(Ph)=C=NCPh3. H-1 dynamic NMR spectroscopy allows the determination of the activation energy of the nitrogen inversion Delta G* = 9.9 +/- 0.2 kcal/mol. In the absence of a trapping reagent, 5 undergoes an elimination of lithium halide with formation of the eight-membered cyclic C,N-bis(germadiyl) bis(ketenimine) 1, which is the first ring containing two ketenimine moieties. 1 has been characterized by IR (nu(C=C=N) 2015 cm(-1)) and C-13 NMR spectroscopy (170.87 ppm for the sp carbon) and by an X-ray structure determination, which displays a "cyclohexane" type structure in a chair conformation.

  DOI：

  10.1021/om971014p