O-fluorocarbonyl-9-fluorenone oxime

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: O-fluorocarbonyl-9-fluorenone oxime
• 英文别名: (Fluoren-9-ylideneamino) carbonofluoridate
• 化学式: C₁₄H₈FNO₂
• 分子量: 241.221
• InChiKey: WEUATQAIOWVQIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-fluorocarbonyl-9-fluorenone oxime 、 乙腈 生成 、 fluoroformyl radical
  参考文献：
  名称：

  Time-Resolved Infrared Study on the Photochemistry of O-Fluoroformyl- and O-Chlorooxalyl-9-fluorenone Oxime:  The Reactivity of the Fluoroformyl Radical in Acetonitrile Solution

  摘要：

  [GRAPHICS]This note describes the photochemistry of O-chlorooxalyl- and O-fluoroformyl-9-fluorenone oxime. The solution photochemistry of both precursors was investigated by time-resolved step/scan FTIR spectroscopy. Experiments on O-chlorooxalyl-9-fluorenone oxime only allowed for detection Of CO2 and bleaching of the precursor, indicating predominant N-O cleavage. The chlorocarbonyl radical, ClCOcenter dot was not detected. In contrast, TRIR investigations on fluoroformyl oxime 2 gave evidence for formation of the fluoroformyl radical FCOcenter dot (3), which rapidly adds to the solvent acetonitrile, yielding a fluoroformyl-functionalized iminyl radical 4. Its reaction with triplet molecular oxygen, on the other hand, is impeded by an activation enthalpy that has been calculated as Delta H-# = 3.2 kcal/mol.

  DOI：

  10.1021/jo052246y
• 作为产物：
  描述：

  甲酰氯氟化物 、 9-芴酮肟 以 四氯化碳 、 甲苯 为溶剂， 以76%的产率得到O-fluorocarbonyl-9-fluorenone oxime
  参考文献：
  名称：

  Time-Resolved Infrared Study on the Photochemistry of O-Fluoroformyl- and O-Chlorooxalyl-9-fluorenone Oxime:  The Reactivity of the Fluoroformyl Radical in Acetonitrile Solution

  摘要：

  [GRAPHICS]This note describes the photochemistry of O-chlorooxalyl- and O-fluoroformyl-9-fluorenone oxime. The solution photochemistry of both precursors was investigated by time-resolved step/scan FTIR spectroscopy. Experiments on O-chlorooxalyl-9-fluorenone oxime only allowed for detection Of CO2 and bleaching of the precursor, indicating predominant N-O cleavage. The chlorocarbonyl radical, ClCOcenter dot was not detected. In contrast, TRIR investigations on fluoroformyl oxime 2 gave evidence for formation of the fluoroformyl radical FCOcenter dot (3), which rapidly adds to the solvent acetonitrile, yielding a fluoroformyl-functionalized iminyl radical 4. Its reaction with triplet molecular oxygen, on the other hand, is impeded by an activation enthalpy that has been calculated as Delta H-# = 3.2 kcal/mol.

  DOI：

  10.1021/jo052246y