N-isopropyl-p-trichloroiminophosphorane | 37596-20-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-isopropyl-p-trichloroiminophosphorane
• 英文别名: Isopropyl-iminophosphorsaeuretrichlorid；Trichloro(propan-2-ylimino)-lambda5-phosphane；trichloro(propan-2-ylimino)-λ5-phosphane
• CAS: 37596-20-6
• 化学式: C₃H₇Cl₃NP
• 分子量: 194.428
• InChiKey: XVDPYDJHLXHXQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-isopropyl-p-trichloroiminophosphorane 、 N,N'-二异丙基碳二亚胺 以 甲苯 为溶剂， 生成 2,2,2-trichloro-N,1,3-tri(propan-2-yl)-1,3,2lambda5-diazaphosphetidin-4-imine
  参考文献：
  名称：

  Catalytic Double-Bond Metathesis without the Transition Metal

  摘要：

  Iminophosphoranes of the type X3P=NR (X=Cl, pyrrolyl; R=alkyl, aryl) catalytically metathesize C=N bonds of carbodiimides via an addition/elimination mechanism that, despite the lack of d orbital participation in P-N bonding, conserves the key features of metal-catalyzed olefin metathesis. Diazaphosphetidine intermediates, produced by the formal [2+2] addition of carbodiimides to the P=N bond, have been isolated and characterized. All phosphorus-containing species in the complex catalytic reaction mixtures have been identified and their origins explained. The kinetics of addition of diisopropylcarbodiimide to Cl3P=NPl and subsequent elimination were studied, and rate constants were determined: k(add)=1.7x10(-3) (+/-0.1x10(-3)) M s(-1) and k(elim)=4.0x10(-4) (+/-0.3x10(-4)) s(-1). The rate of these reactions corresponds well with the observed catalytic TOF of 1.44 TO/P/h.

  DOI：

  10.1021/ja020494v
• 作为产物：
  描述：

  异丙基氨盐酸盐 在 五氯化磷 作用下， 以 1,1,2,2-四氯乙烷 为溶剂， 反应 6.42h， 生成 N-isopropyl-p-trichloroiminophosphorane
  参考文献：
  名称：

  Catalytic Double-Bond Metathesis without the Transition Metal

  摘要：

  Iminophosphoranes of the type X3P=NR (X=Cl, pyrrolyl; R=alkyl, aryl) catalytically metathesize C=N bonds of carbodiimides via an addition/elimination mechanism that, despite the lack of d orbital participation in P-N bonding, conserves the key features of metal-catalyzed olefin metathesis. Diazaphosphetidine intermediates, produced by the formal [2+2] addition of carbodiimides to the P=N bond, have been isolated and characterized. All phosphorus-containing species in the complex catalytic reaction mixtures have been identified and their origins explained. The kinetics of addition of diisopropylcarbodiimide to Cl3P=NPl and subsequent elimination were studied, and rate constants were determined: k(add)=1.7x10(-3) (+/-0.1x10(-3)) M s(-1) and k(elim)=4.0x10(-4) (+/-0.3x10(-4)) s(-1). The rate of these reactions corresponds well with the observed catalytic TOF of 1.44 TO/P/h.

  DOI：

  10.1021/ja020494v