5-TfO-6,9-(Me2S)2-B10H11 | 1607003-70-2

• 英文名称: 5-TfO-6,9-(Me2S)2-B10H11
• 英文别名: 5-TfO-6,9-(Me₂S)₂-B₁₀H₁₁
• CAS: 1607003-70-2
• 化学式: C₅H₂₃B₁₀F₃O₃S₃
• 分子量: 392.539
• InChiKey: ZNTHTFGBPXJGCN-UHFFFAOYSA-N

计算性质

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

• 作为反应物：
  描述：

  5-TfO-6,9-(Me2S)2-B10H11 、 苯乙炔 以 甲苯 为溶剂， 以57%的产率得到1-phenyl-4-TfO-1,2-C₂B₁₀H₁₀
  参考文献：
  名称：

  Synthesis, Structural Characterization, and Reactivity Studies of 5-CF₃SO₃-B₁₀H₁₃

  摘要：

  In contrast to previous reactions carried out in cyclopentane solvent at room temperature that produced 6-TfO-B10H13 (TfO = CF3SO3), the reaction of c/oso-B10H102- with a large excess of trifluoromethanesulfonic acid in the ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate (bmimOTf) gave exclusively the previously unknown S-TfO-B10H13 isomer. Experimental and computational studies demonstrated that the difference in the products of the two reactions is a result of 6-TfO-B10H13 isomerizing to S-TfO-B10H13 above room temperature in bmimOTf solutions. Reactivity studies showed that 5-TfO-B10H13: (1) is deprotonated by reaction with 1,8-bis(dimethylamino)naphthalene to form the S-TfO-B10H121- anion; (2) reacts with alcohols to produce 6-RO-B10H13 boryl ethers (R = Me and 4-CH3O-C6H4); (3) undergoes olefin-hydroboration reactions to form 5-TfO-6,9-R-2-B10H11 derivatives; and (4) forms a 5-TfO-6,9-(Me2S)(2)-B10H11 adduct at its Lewis acidic 6,9-borons upon reaction with dimethylsulfide. The S-TfO-6,9-(Me2S)(2)-B10H11 adduct was also found to undergo alkyne-insertion reactions to form a range of previously unreported triflate-substituted 4-TfO-ortho-carboranes (1-R-4-TfO-1,2-C2B10H10) and reactions with triethylamine or ammonia to form the first TfO-substituted decaborate [R3NH+](2)[2-TfO-B10H92-], and [R3NH+](2)[1-TfO-B10H92-] (R = H, Et) salts.

  DOI：

  10.1021/ic500684b
• 作为产物：
  描述：

  二甲基硫 、 5-TfO-B10H13 以 甲苯 为溶剂， 反应 3.0h， 以70%的产率得到5-TfO-6,9-(Me2S)2-B10H11
  参考文献：
  名称：

  Synthesis, Structural Characterization, and Reactivity Studies of 5-CF₃SO₃-B₁₀H₁₃

  摘要：

  In contrast to previous reactions carried out in cyclopentane solvent at room temperature that produced 6-TfO-B10H13 (TfO = CF3SO3), the reaction of c/oso-B10H102- with a large excess of trifluoromethanesulfonic acid in the ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate (bmimOTf) gave exclusively the previously unknown S-TfO-B10H13 isomer. Experimental and computational studies demonstrated that the difference in the products of the two reactions is a result of 6-TfO-B10H13 isomerizing to S-TfO-B10H13 above room temperature in bmimOTf solutions. Reactivity studies showed that 5-TfO-B10H13: (1) is deprotonated by reaction with 1,8-bis(dimethylamino)naphthalene to form the S-TfO-B10H121- anion; (2) reacts with alcohols to produce 6-RO-B10H13 boryl ethers (R = Me and 4-CH3O-C6H4); (3) undergoes olefin-hydroboration reactions to form 5-TfO-6,9-R-2-B10H11 derivatives; and (4) forms a 5-TfO-6,9-(Me2S)(2)-B10H11 adduct at its Lewis acidic 6,9-borons upon reaction with dimethylsulfide. The S-TfO-6,9-(Me2S)(2)-B10H11 adduct was also found to undergo alkyne-insertion reactions to form a range of previously unreported triflate-substituted 4-TfO-ortho-carboranes (1-R-4-TfO-1,2-C2B10H10) and reactions with triethylamine or ammonia to form the first TfO-substituted decaborate [R3NH+](2)[2-TfO-B10H92-], and [R3NH+](2)[1-TfO-B10H92-] (R = H, Et) salts.

  DOI：

  10.1021/ic500684b