Bis(pentafluorophenyl)diazomethane | 151798-49-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: Bis(pentafluorophenyl)diazomethane
• 英文别名: 1-[Diazo-(2,3,4,5,6-pentafluorophenyl)methyl]-2,3,4,5,6-pentafluorobenzene
• CAS: 151798-49-1
• 化学式: C₁₃F₁₀N₂
• 分子量: 374.14
• InChiKey: QTHRCDBAKSUKOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  2
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Bis(pentafluorophenyl)diazomethane 生成 Bis(pentafluorophenyl)methyl methyl ether
  参考文献：
  名称：

  Tomioka Hideo, Mizutani Kenzoh, Matsumoto Kenji, Hirai Katauyuki, J. Org. Chem, 58 (1993) N 25, S 7128-7134

  摘要：

  DOI：
• 作为产物：
  描述：

  十氟二苯甲醇 在 吡啶 、 silver tetrafluoroborate 、 氯化亚砜 、 potassium tert-butylate 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙酸酐 、 溶剂黄146 为溶剂， 反应 4.02h， 生成 Bis(pentafluorophenyl)diazomethane
  参考文献：
  名称：

  Generation, reactions, direct observation, and kinetics of decafluorodiphenylcarbene

  摘要：

  Bis(pentafluorophenyl)diazomethane (1a) was prepared, and reactivities of perfluorodiphenylcarbene (2a) generated by photolysis of la were investigated not only in terms of product analysis but also by using matrix isolation spectroscopy as well as laser flash photolysis techniques. Product distributions observed in the reactions of 2a in benzene, cyclohexane, and trans-1,2-dichloroethylene suggested that 2a reacted with those substrates with moderate reactivities toward carbene mostly in its singlet state presumably owing to the increased electrophilicity induced by fluorine substituents while the reaction with the alkane C-H bonds in concerted fashion was retarded partly due to steric effect in the singlet state which thus decayed to the triplet states that underwent predominantly H atom abstraction forming tetraarylethane. Photolysis of 1a in Ar matrix at 10 K produced 2a which was observed by IR and UV and shown to react with doped O2 to produce ultimately perfluorobenzoate by way of the carbonyl oxide and dioxirane, both intermediates being characterized by IR and UV/vis spectroscopy. Laser flash photolysis of 1a in acetonitrile solution produced a transient absorption (lambda = 320 nm) due to bis(pentafluorophenyl)methyl radical (14a) obviously produced by H atom abstraction of the triplet 2a, which was trapped by oxygen to generate the carbonyl oxide (11a) showing its absorption maximum at 400 nm (tau = 5 ms) and also by 1,4-cyclohexadiene to form the methyl radical (14a) with the rate constant of 1.1 x 10(7) M-1 s-1. The lifetime of the triplet 2a was estimated to be approximately 1 us.

  DOI：

  10.1021/jo00077a040