(t-Bu)(H)(Ph)B2(trifluoromethanesulfonate)P2(i-Pr)2 | 1189341-55-6

• 英文名称: (t-Bu)(H)(Ph)B2(trifluoromethanesulfonate)P2(i-Pr)2
• 英文别名: cis-(t-Bu)(H)(Ph)B2(OTf)P2(i-Pr)2
• CAS: 1189341-55-6
• 化学式: C₂₃H₄₃B₂F₃O₃P₂S
• 分子量: 540.223
• InChiKey: JRGVPKKUAYLVHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  三氟甲磺酸 、 (t-Bu)(Ph)B2P2(i-Pr)2 以 正戊烷 为溶剂， 以20%的产率得到(t-Bu)(H)(Ph)B2(trifluoromethanesulfonate)P2(i-Pr)2
  参考文献：
  名称：

  Ionic-Type Reactivity of 1,3-Dibora-2,4-diphosphoniocyclobutane-1,3-diyls: Regio- and Stereoselective Addition of Hydracids

  摘要：

  Hydrogen chloride and trifluoromethane sulfonic acid readily add to the symmetrically substituted 1,3-dibora-2,4-diphosphoniocyclobutane-1,3-diyl (1) and unsymmetrically substituted 1,3-dibora-2,4-diphosphoniobicyclo[1.1.0]butane (3) under mild conditions, substantiating some formal analogies between the PBPB diradicaloids D and alkenes. X-ray diffraction analyses carried out on all the resulting 1,3-diborata-2,4-diphosphoniocyclobutanes (2, 4-6) revealed that the reactions proceed with complete stereo- and regio-selectivity, and that an unusual t-Bu -> i-Bu isomerization can occur at boron. DFT calculations shed more light on the factors controlling the regioselectivity of the additions, its concerted versus stepwise character, and support an original two-step mechanism for the t-Bu -> i-Bu isomerization, involving a carbocationic sigma-borane adduct as a key intermediate.

  DOI：

  10.1021/ja903746p