1-fluoro-1,1,2-triphenylethane | 125440-39-3

• 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: 1-fluoro-1,1,2-triphenylethane
• 英文别名: (1-fluoro-1,2-diphenylethyl)benzene
• CAS: 125440-39-3
• 化学式: C₂₀H₁₇F
• 分子量: 276.353
• InChiKey: FTGGRFOAIPEYET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  3,3,3-三苯基丙酸 在 silver fluoride 、 dioxide titanium 作用下， 以 乙腈 为溶剂， 以60%的产率得到1-fluoro-1,1,2-triphenylethane
  参考文献：
  名称：

  Evidence for carbocation intermediates in the titanium dioxide-catalyzed photochemical fluorination of carboxylic acids

  摘要：

  Laser flash photolysis/transient absorbance spectroscopy was used to determine the mechanism of photo-Kolbe fluorination of carboxylic acids, RCOOH --> RF, at colloidal TiO2 suspensions in acetonitrile. Transient absorption spectra of Ph3C+, Ph3C., Ph2CH. and Ph2CH+ were observed from the photooxidation of Ph3CCOOH and Ph2CCOOH at TiO2 using 355-nm excitation. Transient decays, monitored in the presence and absence of fluoride ions, showed that the carbocations reacted rapidly with fluoride, but the neutral radicals did not. By varying the laser intensity, it was found that the photooxidation of Ph3CCOOH to Ph3C. at TiO2 occurred via a single-photon process, while the formation of Ph3C+ required two photons. This finding is in agreement with the parabolic light intensity dependence of initial reaction rates in bulk photolysis experiments. Although fluoride is atrongly adsorbed on the TiO2 surface in acetonitrile solution, the oxidizing power of photogenerated holes could be increased by coordinating HF to F-, and therefore the threshold for oxidative photochemical fluorination was extended to more positive potentials. In this way less easily oxidized carboxylic acids RCOOH could be converted to RF.

  DOI：

  10.1021/jo00058a019

文献信息

• New photochemical method for selective fluorination of organic molecules
  作者：Chong Mou Wang、Thomas E. Mallouk

  DOI：10.1021/ja00161a066

  日期：1990.2