1,2,5,6-tetramethylcyclooctatetraene | 17340-08-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,2,5,6-tetramethylcyclooctatetraene
• 英文别名: 1,2,5,6-Tetramethylcyclooctadien
• CAS: 17340-08-8
• 化学式: C₁₂H₁₆
• 分子量: 160.259
• InChiKey: ACZMPCLZOUDWJX-BDMDMGEZSA-N

物化性质

• 沸点：
  234.7±7.0 °C(Predicted)
• 密度：
  0.856±0.06 g/cm3(Predicted)

反应信息

• 作为产物：
  描述：

  1,2,5,6-tetrakis(bromomethyl)cyclooctatetraene 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以57%的产率得到1,2,5,6-tetramethylcyclooctatetraene
  参考文献：
  名称：

  Two complementary syntheses of symmetrically-tetrasubstituted cyclooctatetraenes

  摘要：

  Two complementary synthetic approaches to tetrasubstituted cyclooctatetraenes (COT's) have been developed. The first approach involves reaction of terminal acetylenes with AlBr3 and Et3N to generate mixtures of 1,3,5,7- and 1,2,5,6-substituted syn-tricyclo[4.2 .0.02,5]octadienes (TCOD's) in satisfactory yield. These TCOD's can then be thermally or photolytically ring opened to 1,3,5,7- and 1,2,5,6-substituted COT's. Bulky substituents (e.g., tert-butyl, isopropyl) give exclusively 1,3,5,7-substituted TCOD and COT products. In the second approach, 1,3,5,7- (5) and 1,2,5,6-tetrakis-(hydroxymethyl)COT's (6) were generated and isolated in good yield from the Ni(0)-catalyzed tetramerization of propargyl alcohol. These isomers were converted to their corresponding tetrakis-(bromomethyl)COT's 8 and 9. Reduction of 8 and 9 with LiAlH4 afforded 1,3,5,7-tetramethylCOT (10) and 1,2,5,6-tetramethylCOT (11).

  DOI：

  10.1021/jo00061a007