Difluoropropadienone | 119820-21-2

• 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: Difluoropropadienone
• 英文别名: Difluoropropadien-1-one
• CAS: 119820-21-2
• 化学式: C₃F₂O
• 分子量: 90.0292
• InChiKey: FKUIFZADSXCJOC-UHFFFAOYSA-N

物化性质

• 沸点：
  -4.4±35.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  6
• 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：

  Difluoropropadienone 在 氮气 作用下， 以 solid matrix 为溶剂， 生成 一氧化碳 、 Difluorodiazoethene
  参考文献：
  名称：

  Difluoropropadienone as a source of difluorovinylidene and difluorodiazoethene

  摘要：

  DOI：

  10.1021/ja00166a056
• 作为产物：
  描述：

  Difluorocyclopropenone 生成 Difluoropropadienone
  参考文献：
  名称：

  BRAHMS, JOHN C.;DAILEY, WILLIAM P., J. AMER. CHEM. SOC., 111,(1989) N4, C. 8940-8941

  摘要：

  DOI：

文献信息

• Difluoromaleic anhydride as a source of matrix isolated difluoropropadienone, difluorocyclopropenone and difluoroacetylene
  作者：John C. Brahms、William P. Dailey

  DOI：10.1021/ja00206a039

  日期：1989.11

  A 240 nm, reaction de la difluoro-3,4 dihydro-2,5 furannedione-2,5. Obtention de la difluoro-2,3 cyclopropenone, du difluoro acetylene et de la difluoro-3,3 propanedienone

  A 240 nm，反应 de la difluoro-3,4 dihydro-2,5 furannedione-2,5。获得 de la difluoro-2,3 cyclopropenone, du difluoroacetylene et de la difluoro-3,3 propanedienone
• Squaric acid difluoride
  作者：Michael Senzlober、Hans Bürger、Reint Eujen、Achim Gelessus、Walter Thiel

  DOI：10.1016/s0022-1139(99)00138-4

  日期：1999.11

  Hitherto unknown squaric acid difluoride (3,4-difluoro-3-cyclobutene-1,2-dione) (1a) has been synthesized in 71% yield by gas phase fluorination of squaric acid dichloride (1c) with KF at 250 degrees C. (1a) has been characterized by multinuclear NMR, mass, IR and Raman spectra. The IR spectrum is in excellent agreement with its ab initio prediction (MP2, 6-311 + G(2d, p)). The vacuum thermolysis of (1a) at 700 degrees C does not yield the expected decarbonylation product FCCF (2a) although the precursor of the latter, F2CCCO, and three C3F4 isomers (propyne, allene, cyclopropene) which are also found as decomposition products of (2a) have been identified. (C) 1999 Elsevier Science S.A. All rights reserved.
• Synthesis of difluoropropadienone
  作者：John C. Brahms、William P. Dailey

  DOI：10.1021/ja00190a055

  日期：1989.4
• 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.
• 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