Trifluoro-methanesulfonate2,4,6,8-tetra-tert-butyl-5-methyl-1,3,7-triphospha-5-phosphonia-cubane; | 141556-31-2

• 分子结构分类: 有机化合物
• 英文名称: Trifluoro-methanesulfonate2,4,6,8-tetra-tert-butyl-5-methyl-1,3,7-triphospha-5-phosphonia-cubane
• CAS: 141556-31-2
• 化学式: CF₃O₃S*C₂₁H₃₉P₄
• 分子量: 564.506
• InChiKey: YHSJVYVJQUXFSP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  9.0
• 重原子数：
  33.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2,4,6,8-tetra-tert-butyl-1,3,5,7-tetraphosphapentacyclo<4.2.0.0^2,5.0^3,8.0^4,7>octane 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 反应 96.0h， 以95%的产率得到Trifluoro-methanesulfonate2,4,6,8-tetra-tert-butyl-5-methyl-1,3,7-triphospha-5-phosphonia-cubane;
  参考文献：
  名称：

  Phosphorus compounds. Part 68. Tetraphosphacubane chemistry: probing phosphorus reactivity by protonation, alkylation, and alkynylation. Formation of novel phosphonium di- and monocations in superacid media and monocations with super electrophiles

  摘要：

  Tetra-tert-butyltetraphosphacubane (1) is diprotonated with FSO3H.SbF5 (1: 1) (Magic acid)/SO2 at two of the four equivalent phosphorus atoms to give a persistent diphosphonium cation 2. In FSO3H/SO2 or CF3SO3H (TfOH)/SO2 Only the monoprotonated phosphonium ion 4 was observed. Upon exothermic quenching of the Magic acid solutions of 2 apart from intact 1, oxotetraphosphacubane 3 was formed. Quenching of the FSO3H or TfOH solutions of 4 (no SbF5) gave intact 1 together with traces of 3. Ambient reactions of 1 with methyl triflate, trimethyloxonium tetrafluoroborate and with (trimethylsilyl)methyl triflate led to monoalkylation at phosphorus (steps 4-6, Scheme 1). Reaction of 1 with propene/TfOH as an iPr+ source gave the monocation 8 (P-31 NMR) in competition with extensive olefin oligomerization. Crowded triisopropylsilyl triflate did not react with 1 even under forcing conditions. Similar reactions of 1 with alkynyl(phenyl)iodonium triflates led to monoalkynylation at phosphorus (step 8, Scheme I).

  DOI：

  10.1021/jo00067a051

文献信息

• Birkel, Manfred; Schulz, Joachim; Bergstraesser, Uwe, Angewandte Chemie, 1992, vol. 104, # 7, p. 870 - 873
  作者：Birkel, Manfred、Schulz, Joachim、Bergstraesser, Uwe、Regitz, Manfred

  DOI：——

  日期：——