二氟乙烯酮 | 683-54-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 中文名称: 二氟乙烯酮
• 中文别名: 全氟乙烯酮；2,2-二氟乙烯-1-酮
• 英文名称: Perfluoroketene
• 英文别名: Difluoroketene；Difluoroacetyl
• CAS: 683-54-5
• 化学式: C₂F₂O
• 分子量: 78.0182
• InChiKey: OTTXCOAOKOEENK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二氟乙烯酮 生成 二氟卡宾
  参考文献：
  名称：

  Oxidation of Difluorovinylidene

  摘要：

  Difluorovinylidene is a highly reactive and extremely electrophilic singlet carbene that thermally abstracts an oxygen atom from CO2 at temperatures as low as 30 K. The resulting difluoroketene is characterized for the first time using IR spectroscopy in combination with isotopic labeling and density functional theory (DFT) calculations. The three observed IR absorptions of the ketene at 1274, 1427, and 2162 cm(-1) are assigned to the asymmetrical FCF stretching vibration and the asymmetrical and symmetrical CCO stretching vibrations, respectively. The oxidation of difluorovinylidene with O-3(2) results in a complex product mixture with CF2, C2F4, CO2, COF2, and CO as the major products. A mechanism consistent with all observed products is proposed.

  DOI：

  10.1002/(sici)1521-3765(19980904)4:9<1611::aid-chem1611>3.0.co;2-3
• 作为产物：
  描述：

  poly(vinylidene fluoride) 在 二氧化碳 作用下， 以 solid matrix 为溶剂， 生成 二氟乙烯酮
  参考文献：
  名称：

  Reactions of Difluorovinylidene—A Super-Electrophilic Carbene

  摘要：

  Difluorovinylidene is the only vinylidene that could be isolated in low temperature matrices, so far, Its unusual reactivity is governed by its extreme electrophilicity and electron affinity, Thus, it not only adds CO and N without difficulties, but also inserts into CH4 and even H-2 at temperatures below 40 K. The reaction of F2C=C: with FC=CF clearly reveals that the formation of methylenecyclopropene proceeds in a stepwise reaction, The most striking example for the electrophilicity of F2C=C: is the thermal reaction with Xe to give a charge-transfer complex with a characteristic IR spectrum.

  DOI：

  10.1002/(sici)1521-3765(19990104)5:1<24::aid-chem24>3.0.co;2-z

文献信息

• MALHERBE, R.;RIST, G.;BELLUS, D., J. ORG. CHEM., 1983, 48, N 6, 860-869
  作者：MALHERBE, R.、RIST, G.、BELLUS, D.

  DOI：——

  日期：——
• Reactions of Difluorovinylidene—A Super-Electrophilic Carbene
  作者：Wolfram Sander、Carsten Kötting

  DOI：10.1002/(sici)1521-3765(19990104)5:1<24::aid-chem24>3.0.co;2-z

  日期：1999.1.4

  Difluorovinylidene is the only vinylidene that could be isolated in low temperature matrices, so far, Its unusual reactivity is governed by its extreme electrophilicity and electron affinity, Thus, it not only adds CO and N without difficulties, but also inserts into CH4 and even H-2 at temperatures below 40 K. The reaction of F2C=C: with FC=CF clearly reveals that the formation of methylenecyclopropene proceeds in a stepwise reaction, The most striking example for the electrophilicity of F2C=C: is the thermal reaction with Xe to give a charge-transfer complex with a characteristic IR spectrum.
• Oxidation of Difluorovinylidene
  作者：Carsten Kötting、Wolfram Sander、Michael Senzlober、Hans Bürger

  DOI：10.1002/(sici)1521-3765(19980904)4:9<1611::aid-chem1611>3.0.co;2-3

  日期：1998.9.4

  Difluorovinylidene is a highly reactive and extremely electrophilic singlet carbene that thermally abstracts an oxygen atom from CO2 at temperatures as low as 30 K. The resulting difluoroketene is characterized for the first time using IR spectroscopy in combination with isotopic labeling and density functional theory (DFT) calculations. The three observed IR absorptions of the ketene at 1274, 1427, and 2162 cm(-1) are assigned to the asymmetrical FCF stretching vibration and the asymmetrical and symmetrical CCO stretching vibrations, respectively. The oxidation of difluorovinylidene with O-3(2) results in a complex product mixture with CF2, C2F4, CO2, COF2, and CO as the major products. A mechanism consistent with all observed products is proposed.