2,3,5-tribromodiazocyclopentadiene | 847054-06-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物
• 英文名称: 2,3,5-tribromodiazocyclopentadiene
• 英文别名: 1,2,4-tribromo-5-diazocyclopenta-1,3-diene
• CAS: 847054-06-2
• 化学式: C₅HBr₃N₂
• 分子量: 328.788
• InChiKey: YOPUJBGELPOQMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.4
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  五羰基溴化锰(I) 、 2,3,5-tribromodiazocyclopentadiene 以 further solvent(s) 为溶剂， 以85%的产率得到(η5-tetrabromocyclopentadienyl)tricarbonylmanganese
  参考文献：
  名称：

  Syntheses and structures of missing links among polybromocyclopentadienyl rhenium and manganese tricarbonyl complexes

  摘要：

  Reactions of diazocyclopentacliene and NBS at appropriate stoichiometries give 2,5-dibromodiazocyclopentadiene and 2,3,5-tribromodiazocyclopentadiene in 40% and 30% yields, respectively, after chromatography. These react with BrRe(CO)(5) or BrMn(CO)(5) (80degreesC, CF3C6H5) to give (eta(5)-1 2,3-C5HBr3)M(CO)(3) (3; M = a, Re; b, Mn) and (eta(5) -C5HBr4)M(CO)(3) (4a,b) in 75-85% yields. In the case of 4a, the intermediate ill-cyclopentadienyl complex (eta(1)-C5HBr4)Re(CO)(5) (4'a) can be isolated (44%). An isomer of 3b, (eta(5)- 1,2,4-C5H2Br3)Mn(CO)(3), is accessed by desilylating previously reported (eta(5)-1,2,4-C-5(SiMe3)(2)Br-3)Mn(CO)(3) with CsF/MeOH (85%). The reaction of tetrabromodiazocyclopentadiene and BrRe(CO)(5) at 80degreesC in CF3C6H5 gives the eta(1)-cyclopentadienyl complex (eta(1) -C5Br5)Re(CO)(5) (5'a, 74%) which cannot be induced to decarbonylate to (eta(5) -C5Br5)Re(CO)(3) (5a) under a variety of conditions. However, 5a can be isolated (45%) when a similar reaction is conducted at 120degreesC. The IR properties of the preceding complexes are compared, and the crystal structures of 3a, 3b, 5a, and 5'a are determined and analyzed. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.09.072
• 作为产物：
  描述：

  5-重氮基环戊并-1,3-二烯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 丙酮 为溶剂， 以30%的产率得到2,3,5-tribromodiazocyclopentadiene
  参考文献：
  名称：

  Syntheses and structures of missing links among polybromocyclopentadienyl rhenium and manganese tricarbonyl complexes

  摘要：

  Reactions of diazocyclopentacliene and NBS at appropriate stoichiometries give 2,5-dibromodiazocyclopentadiene and 2,3,5-tribromodiazocyclopentadiene in 40% and 30% yields, respectively, after chromatography. These react with BrRe(CO)(5) or BrMn(CO)(5) (80degreesC, CF3C6H5) to give (eta(5)-1 2,3-C5HBr3)M(CO)(3) (3; M = a, Re; b, Mn) and (eta(5) -C5HBr4)M(CO)(3) (4a,b) in 75-85% yields. In the case of 4a, the intermediate ill-cyclopentadienyl complex (eta(1)-C5HBr4)Re(CO)(5) (4'a) can be isolated (44%). An isomer of 3b, (eta(5)- 1,2,4-C5H2Br3)Mn(CO)(3), is accessed by desilylating previously reported (eta(5)-1,2,4-C-5(SiMe3)(2)Br-3)Mn(CO)(3) with CsF/MeOH (85%). The reaction of tetrabromodiazocyclopentadiene and BrRe(CO)(5) at 80degreesC in CF3C6H5 gives the eta(1)-cyclopentadienyl complex (eta(1) -C5Br5)Re(CO)(5) (5'a, 74%) which cannot be induced to decarbonylate to (eta(5) -C5Br5)Re(CO)(3) (5a) under a variety of conditions. However, 5a can be isolated (45%) when a similar reaction is conducted at 120degreesC. The IR properties of the preceding complexes are compared, and the crystal structures of 3a, 3b, 5a, and 5'a are determined and analyzed. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.09.072