triphenyl(prop-1-ynyl)phosphonium bromide | 54599-98-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: triphenyl(prop-1-ynyl)phosphonium bromide
• 英文别名: Triphenyl(prop-1-yn-1-yl)phosphanium bromide；triphenyl(prop-1-ynyl)phosphanium;bromide
• CAS: 54599-98-3
• 化学式: Br*C₂₁H₁₈P
• 分子量: 381.252
• InChiKey: LWUVYOTWNWUXTI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.97
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  triphenyl(prop-1-ynyl)phosphonium bromide 以 二氯甲烷 、 水 为溶剂， 生成 [platinum(η²-C(CH3)CPPh3)(PPh3)2](hexafluorophosphate)
  参考文献：
  名称：

  η²-Allenyl- and η²-Alkynylphosphonium Complexes of Platinum

  摘要：

  The reaction of the propargylic salt [Ph3PCH2C CH]PF6 with [Pt(C2H4)(PPh3)(2)] affords the eta(2)-allenylphosphonium salt [Pt(eta(2)-CH2=C=CHPPh3)(PPh3)(2)]PF6 via a metal-mediated propargylic rearrangement. Isomerization of the complex occurs in solution to generate the salt [Pt{eta(2)-C(PPh3)=C=CH2}(PPh3)(2)]PF6, wherein the allene is coordinated by the internal C=C bond. Computational studies indicate that the isomerization of the propargylic cation [Ph3PCH2C CH](+) to the allenyl species [Ph3PCH=C=CH2](+) and the alpha-alkynyl isomer [Ph3PC CCH3](+) is thermodynamically favorable. The isomeric eta(2)-alkynylphosphonium salt [Pt{eta(2)-C(CH3)=CPPh3}(PPh3)(2)]PF6 is formed from the reaction of [Ph3PC CCH3]PF6 with [Pt(C2H4)(PPh3)(2)] and does not isomerize to the propargylic or allenyl-forms.

  DOI：

  10.1021/om400406s
• 作为产物：
  描述：

  炔丙基三苯基溴化膦 以 乙腈 为溶剂， 反应 17.0h， 生成 triphenyl(prop-1-ynyl)phosphonium bromide
  参考文献：
  名称：

  Synthesis and transformations of triphenylpropargylphosphonium bromide

  摘要：

  A method of the s,mthesis of triphenylpropargylphosphonium bromide is developed. Its isomerization and hydration in various solvents are studied, and reactions with secondary arnines, tricthylamine, and triphenylphosphine are carried out. It is established that secondary arnines add to the intermediate allene isomer with subsequent migration ofthe formed double bond to the phosphorus atorn. The reaction of triethylamine with trir.henylpropargyl and triphenylethynyl bromides occurs similarly to alkaline hydrolysis involving attack of' the amine on the phosphorus atom. Triphenylphosphine fornis with triphenylpropar-ylphosphonium biomide a bis-salt with a terminal methylene group. Experimental evidence is obtained showinc -, that for plioi;phoxazole derivatives to form from oxiines derived from triphenyl(oxomethyl)phosphonium salts tha latter should bear an aryl substituent at the keto group.

  DOI：

  10.1134/s1070363208060133

文献信息

• Synthesis and transformations of triphenylpropargylphosphonium bromide
  作者：G. B. Bagdasaryan、P. S. Pogosyan、G. A. Panosyan、M. G. Indzhikyan

  DOI：10.1134/s1070363208060133

  日期：2008.6

  A method of the s,mthesis of triphenylpropargylphosphonium bromide is developed. Its isomerization and hydration in various solvents are studied, and reactions with secondary arnines, tricthylamine, and triphenylphosphine are carried out. It is established that secondary arnines add to the intermediate allene isomer with subsequent migration ofthe formed double bond to the phosphorus atorn. The reaction of triethylamine with trir.henylpropargyl and triphenylethynyl bromides occurs similarly to alkaline hydrolysis involving attack of' the amine on the phosphorus atom. Triphenylphosphine fornis with triphenylpropar-ylphosphonium biomide a bis-salt with a terminal methylene group. Experimental evidence is obtained showinc -, that for plioi;phoxazole derivatives to form from oxiines derived from triphenyl(oxomethyl)phosphonium salts tha latter should bear an aryl substituent at the keto group.
• η²-Allenyl- and η²-Alkynylphosphonium Complexes of Platinum
  作者：Annie L. Colebatch、Ian A. Cade、Anthony F. Hill、Mohan M. Bhadbhade

  DOI：10.1021/om400406s

  日期：2013.9.9

  The reaction of the propargylic salt [Ph3PCH2C CH]PF6 with [Pt(C2H4)(PPh3)(2)] affords the eta(2)-allenylphosphonium salt [Pt(eta(2)-CH2=C=CHPPh3)(PPh3)(2)]PF6 via a metal-mediated propargylic rearrangement. Isomerization of the complex occurs in solution to generate the salt [Pteta(2)-C(PPh3)=C=CH2}(PPh3)(2)]PF6, wherein the allene is coordinated by the internal C=C bond. Computational studies indicate that the isomerization of the propargylic cation [Ph3PCH2C CH](+) to the allenyl species [Ph3PCH=C=CH2](+) and the alpha-alkynyl isomer [Ph3PC CCH3](+) is thermodynamically favorable. The isomeric eta(2)-alkynylphosphonium salt [Pteta(2)-C(CH3)=CPPh3}(PPh3)(2)]PF6 is formed from the reaction of [Ph3PC CCH3]PF6 with [Pt(C2H4)(PPh3)(2)] and does not isomerize to the propargylic or allenyl-forms.