1,1-dideutero-2,3,4,5-tetraphenyl-1-germacyclopenta-2,4-diene | 857907-00-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,1-dideutero-2,3,4,5-tetraphenyl-1-germacyclopenta-2,4-diene
• 英文别名: dideuterogermole
• CAS: 857907-00-7
• 化学式: C₂₈H₂₂Ge
• 分子量: 433.057
• InChiKey: DVMLAWQLDQFHRN-DNBURNPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  lithium aluminium deuteride 、 1,1-dichloro-2,3,4,5-tetraphenyl-1-germacyclopenta-2,4-diene 以 四氢呋喃 为溶剂， 以52%的产率得到1,1-dideutero-2,3,4,5-tetraphenyl-1-germacyclopenta-2,4-diene
  参考文献：
  名称：

  Syntheses of Oligometalloles by Catalytic Dehydrocoupling

  摘要：

  The dehydrocoupling polycondensation of dihydro(tetraphenyl)metalloles (M = Si or Ge) with 0.2 mol % H(2)PtCl(6)center dot xH(2)O and excess cyclohexene produces the respective oligometallole in high yield (> 80%), where every silicon or germanium atom of the oligomer backbone is part of a silole or germole ring. Slightly less reactive catalyst systems of 1 mol % of Wilkinson's catalyst, (RhCl(PPh(3))(3)), or Pd(PPh(3))(4) yield the respective oligometallole in good yield (similar to 60%). With these latter systems, and under less vigorous reflux conditions, the (tetraphenyl)silole dimer may be isolated in 40% yield. X-ray structural characterization of the dimer reveals a Si-Si bond length of 2.363(2) angstrom and an H-Si-Si-H torsion angle of 90(2)degrees. Using excess cyclohexene as a coreagent with RhCl(PPh(3))(3) increases the yield of oligomer and also eliminates dimer byproduct. The methyl-terminated dimer forms in the reaction between H(2)PtCl(6)center dot xH(2)O and methylhydro(tetraphenyl)silole, but not in the similar reaction with the Rh and Pd catalysts. The methyl-terminated dimer has a Si-Si bond length of 2.375(1) angstrom and an H-Si-Si-H torsion angle of 92.3(1)degrees. Additionally, the oligosilole may be prepared by placing 1:2 dihydrosilole/cyclohexene and I mol % Wilkinson's catalyst in an Emrys Optimizer microwave synthesizer for 2 h. The molecular weight (M(w)) of the oligometalloles ranges from 3000 to 7000. Even though the metallole possesses a secondary metalloid atom and contains bulky phenyl groups, polymerization may occur because the tetraphenylmetallole monomers have small angles at C-M-C (93.21 degrees on C-Si-C and 90.14 degrees on C-Ge-C), resulting in less steric hindrance at the metalloid center. Oligo(tetraphenyl)germole exhibits an absorption at 378 nm (is an element of = 5400 L/mol Ge(.)cm). The germole is photoluminescent in toluene solution, emitting blue-green light (498 nm, Phi = 0.01). The hydrogen-terminated silole dimer shows a similar UV-vis absorption at 372 nm (is an element of = 9600 L/mol(.)cm) and luminesces green at 506 nm (Phi = 0.007). The methyl-terminated dimer absorbs at 370 nm (is an element of = 11800 L/mol(.)cm) and luminesces blue at 468 nm (Phi = 0.004).

  DOI：

  10.1021/om0490886