(2-fluorophenylimino)tri(1-pyrrolyl)-phosphorane

• 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: (2-fluorophenylimino)tri(1-pyrrolyl)-phosphorane
• 英文别名: N-2-fluorophenyl-p-trispyrrolyliminophosphorane；(2-Fluorophenylimino)tripyrrolylphosphorane；(2-fluorophenyl)imino-tri(pyrrol-1-yl)-λ5-phosphane
• 化学式: C₁₈H₁₆FN₄P
• 分子量: 338.324
• InChiKey: UTRPXBSGGACRPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  27.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氟苯胺盐酸盐 在 五氯化磷 作用下， 以 正己烷 、 1,1,2,2-四氯乙烷 为溶剂， 反应 14.5h， 生成 (2-fluorophenylimino)tri(1-pyrrolyl)-phosphorane
  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

文献信息

• (2-Fluorophenylimino)tri(1-pyrrolyl)phosphorane
  作者：Stephen A. Bell、Tara Y. Meyer、Steven J. Geib

  DOI：10.1107/s0108270101013877

  日期：2001.11.15

  The P atom of the title compound, C18H16FN4P, has a slightly distorted tetrahedral geometry. The P-N bond lengths range from 1.671 (3) to 1.680 (3) Angstrom, while the P=N bond is 1.517 (3) Angstrom. The pyrrolyl groups are arranged around the P atom in a chiral propeller-like geometry.