| 148807-60-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 148807-60-7
• 化学式: C₁₆H₂₉BO
• 分子量: 248.217
• InChiKey: BSTYMQLSYUHNTG-QXMHVHEDSA-N

反应信息

• 作为产物：
  描述：

  1,3,5-heptatrienyldipropylborane 、 2,4,6-heptatrienyldipropylborane 在 丙酮 作用下， 生成
  参考文献：
  名称：

  2,4,6-庚三烯基二丙基硼烷中的一系列σ重排。1,3-硼转移促进1,7-氢转移的动力学研究

  摘要：

  The dynamic behavior of a novel polyunsaturated allylic borane, 2,4,6-heptatrienyldipropylborane, 5, was studied by NMR spectroscopy. It was found that four geometric isomers 5a-d interconvert reversibly via successive 1,3 sigmatropic shifts of boron (BPr2 group). Due to the thermal 1,7-hydrogen shift occurring in the minor Z,Z-isomer, 5d, the allylic borane 5 is converted stereoselectively and reversibly into the vinylic (E,Z,Z)-1,3,5-heptatrienyldipropylborane, 8. The final equilibrium mixture contains 92% 8 and 8% 5. The effective activation energy of the conversion of 5 into 8 and the activation energy for the reverse reaction were found to be 79.8 and 87.1 kJ/mol, respectively; the preexponential factors proved to be the same, 4.10(8) s-1. Reaction of 5 with cyclopentanone gives the trans-homoallylic alcohol 15a, while 8 reacts with cyclopentanone yielding (Z,Z)-1,3,5-heptatriene, 18.

  DOI：

  10.1021/om00031a019