di-p-tolylphosphanylethyne | 1448222-78-3

• 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: di-p-tolylphosphanylethyne
• 英文别名: Ethynyl-bis(4-methylphenyl)phosphane；ethynyl-bis(4-methylphenyl)phosphane
• CAS: 1448222-78-3
• 化学式: C₁₆H₁₅P
• 分子量: 238.269
• InChiKey: AFLCPHBCKFOFGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  di-p-tolylphosphanylethyne 以 甲苯 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Reaction of Diphenylphosphanylacetylene with RB(C₆F₅)₂ Reagents: Evidence for a Remarkable Sequence of Synergistic Frustrated Lewis Pair Addition Reactions

  摘要：

  Diphenylphosphanylethyne (3a) reacts with tris(pentafluorophenyl)borane at room temperature by a typical frustrated Lewis pair (FLP) reaction. It undergoes a sequential series of 1,2-phosphane/borane additions to the alkyne unit in an overall 2:2 molar ratio to selectively form the dimeric product 5a. Product 5 features a pentafulvene-reminiscent structure with a pair of phosphonium units in the ring and B(C6F5)(3) substituents at the periphery. At elevated temperature, the reaction becomes less selective, now favoring the formation of cis- and trans-1,1-carboboration products from a 1:1 stoichiometry. After photolytic trans/cis isomerization, the vicinal FLP 6a becomes the major product, featuring an intramolecular P center dot center dot center dot B interaction. The reaction of 3a with H3CB(C6F5)(2) also gives a heterocyclic dimer (11), except that here a substituent H/CH3 exchange by an addition/elimination pathway has taken place. In the B(C6F5)(3)-derived system, we were able to trap an alleged intermediate of this rearrangement reaction by adding n-butyl isocyanide. Five products in the Ph2P- and (p-tolyl)(2)P-derived systems were characterized by X-ray diffraction

  DOI：

  10.1021/ic402139g
• 作为产物：
  描述：

  P,P-双(4-甲基苯基)-氯化膦 氯二对甲苯基膦 在 甲醇 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 di-p-tolylphosphanylethyne
  参考文献：
  名称：

  Reaction of Diphenylphosphanylacetylene with RB(C₆F₅)₂ Reagents: Evidence for a Remarkable Sequence of Synergistic Frustrated Lewis Pair Addition Reactions

  摘要：

  Diphenylphosphanylethyne (3a) reacts with tris(pentafluorophenyl)borane at room temperature by a typical frustrated Lewis pair (FLP) reaction. It undergoes a sequential series of 1,2-phosphane/borane additions to the alkyne unit in an overall 2:2 molar ratio to selectively form the dimeric product 5a. Product 5 features a pentafulvene-reminiscent structure with a pair of phosphonium units in the ring and B(C6F5)(3) substituents at the periphery. At elevated temperature, the reaction becomes less selective, now favoring the formation of cis- and trans-1,1-carboboration products from a 1:1 stoichiometry. After photolytic trans/cis isomerization, the vicinal FLP 6a becomes the major product, featuring an intramolecular P center dot center dot center dot B interaction. The reaction of 3a with H3CB(C6F5)(2) also gives a heterocyclic dimer (11), except that here a substituent H/CH3 exchange by an addition/elimination pathway has taken place. In the B(C6F5)(3)-derived system, we were able to trap an alleged intermediate of this rearrangement reaction by adding n-butyl isocyanide. Five products in the Ph2P- and (p-tolyl)(2)P-derived systems were characterized by X-ray diffraction

  DOI：

  10.1021/ic402139g

文献信息

• Redox-Induced Reversible PP Bond Formation to Generate an Organometallic σ⁴λ⁴-1,2-Biphosphane Dication
  作者：Ayham Tohmé、Guillaume Grelaud、Gilles Argouarch、Thierry Roisnel、Stéphanie Labouille、Duncan Carmichael、Frédéric Paul

  DOI：10.1002/anie.201208682

  日期：2013.4.15

  diphosphonium bis(alkynyl) complexes are formed by oxidation of the corresponding FeII alkynyl phosphine complexes. The structure of these organometallic diphosphonium salts and their monomeric precursors were established by X‐ray crystallography. The PP bond can be cleaved by two‐electron reduction to regenerate the monomers.

  两次乐趣：通过氧化相应的Fe II炔基膦配合物形成二聚Fe II二di双（炔基）配合物。这些有机金属二phosph盐及其单体前体的结构是通过X射线晶体学确定的。在P  P键可以由两个电子还原裂解来再生单体。
• Reaction of Diphenylphosphanylacetylene with RB(C₆F₅)₂ Reagents: Evidence for a Remarkable Sequence of Synergistic Frustrated <i>Lewis</i> Pair Addition Reactions
  作者：Jiangang Yu、Gerald Kehr、Constantin G. Daniliuc、Gerhard Erker

  DOI：10.1021/ic402139g

  日期：2013.10.7

  Diphenylphosphanylethyne (3a) reacts with tris(pentafluorophenyl)borane at room temperature by a typical frustrated Lewis pair (FLP) reaction. It undergoes a sequential series of 1,2-phosphane/borane additions to the alkyne unit in an overall 2:2 molar ratio to selectively form the dimeric product 5a. Product 5 features a pentafulvene-reminiscent structure with a pair of phosphonium units in the ring and B(C6F5)(3) substituents at the periphery. At elevated temperature, the reaction becomes less selective, now favoring the formation of cis- and trans-1,1-carboboration products from a 1:1 stoichiometry. After photolytic trans/cis isomerization, the vicinal FLP 6a becomes the major product, featuring an intramolecular P center dot center dot center dot B interaction. The reaction of 3a with H3CB(C6F5)(2) also gives a heterocyclic dimer (11), except that here a substituent H/CH3 exchange by an addition/elimination pathway has taken place. In the B(C6F5)(3)-derived system, we were able to trap an alleged intermediate of this rearrangement reaction by adding n-butyl isocyanide. Five products in the Ph2P- and (p-tolyl)(2)P-derived systems were characterized by X-ray diffraction