Difluorodiazoethene | 110785-07-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: Difluorodiazoethene
• 英文别名: 2-diazo-1,1-difluoroethene
• CAS: 110785-07-4
• 化学式: C₂F₂N₂
• 分子量: 90.0322
• InChiKey: IAPFIWKNBGWEOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  6.0
• 可旋转键数：
  0.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.4
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  Difluorodiazoethene 生成 1,2-二氟乙炔
  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
• 作为产物：
  描述：

  poly(vinylidene fluoride) 在 氮 作用下， 生成 Difluorodiazoethene
  参考文献：
  名称：

  超亲电子卡宾和亲合力的概念

  摘要：

  计算了许多卡宾的电子亲和力和电离势，并与 Moss 定义的卡宾亲和量表 mCXY 进行了比较。建议使用二维而不是一维尺度对卡宾进行分类。电子亲和力高于 2 eV 的极亲电子卡宾的例子是具有单重基态的二氟亚乙烯基和具有三重基态的 4-氧代-2,3,5,6-四氟环己基-2,5-二亚乙烯基。讨论了这些卡宾在基质分离条件下对小分子的反应性。版权所有 © 2000 John Wiley & Sons, Ltd.

  DOI：

  10.1002/1099-1395(200010)13:10<561::aid-poc239>3.0.co;2-u

文献信息

• 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.
• Difluoropropadienone as a source of difluorovinylidene and difluorodiazoethene
  作者：John C. Brahms、William P. Dailey

  DOI：10.1021/ja00166a056

  日期：1990.5
• Difluorovinylidene, F2CC:
  作者：Jürgen Breidung、Hans Bürger、Carsten Kötting、Rodion Kopitzky、Wolfram Sander、Michael Senzlober、Walter Thiel、Helge Willner

  DOI：10.1002/anie.199719831

  日期：1997.10.2

  An alkyne–vinylidene isomerization is also possible with the difluoro compounds 1 and 2! Irradiation of 2 (λ = 193 nm) in an Ar matrix yields 1 exclusively. The IR spectrum agrees with results of novel abinitio calculations, which also suggest that 1—in sharp contrast to the vinylidenes RHCC—is protected against isomerization into 2 by a kinetic barrier. Irradiation with light with λ > 230nm converts 1 back into 2. Already at 35–42 K 1 adds CO and N2 to yields F2CCCO and F2CCNN, respectively. equation image