1,2-Difluoropropylbenzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-Difluoropropylbenzene
• 化学式: C₉H₁₀F₂
• 分子量: 156.175
• InChiKey: GIIKAJTZYTYRHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1,2-Difluoropropylbenzene 在 二氟代氙 作用下， 以 二氯甲烷 为溶剂， 生成 1,2-dichloro-1-phenylpropane
  参考文献：
  名称：

  在顺式和反式-1-苯丙烯中自由基加二氟化氙：与三氯胺和二氯化碘苯的比较

  摘要：

  我们想报告支持有机溶剂中二氟化氙（XeF 2）与烯烃反应的自由基途径的数据。已经提出了自由基中间体用于XeF 2与双键的反应。例如，有人提出了XeF 2气相反应生成乙烯和丙烯的自由基途径[1]。Zupan推测了XeF 2与烯烃的酸催化反应的自由基阳离子途径，但没有提供有关该机理的实验证据[2,3]。填料[4]证明了XeF 2与芳烃反应的自由基阳离子中间体。酸催化的不饱和烃离子反应已有综述[5]。

  DOI：

  10.1016/s0022-1139(00)84013-0
• 作为产物：
  描述：

  甲基苯乙烯 在 氢氟酸 二氟代氙 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 1,2-Difluoropropylbenzene
  参考文献：
  名称：

  Fluorination with XeF2. Part 40. The Important Role of .pi.-Bond Disruption in Fluorine Addition to Phenyl-Substituted Alkenes

  摘要：

  Ionization potentials (IP) for 11 mono- and alpha,alpha-diphenyl-substituted acyclic and cyclic alkenes 1-11 were measured under the same conditions, using a mass spectrometric technique and applying electron impact ionization. The values, ranging from 8.68 eV for styrene (1) to as low as 7.67 eV for 1,2-dihydro-4-phenylnaphthalene (10), were correlated with the logarithms of the relative rates (k(rel), relative to 1,1-diphenylethene) of fluorine addition across the carbon-carbon double bond in HF-catalyzed reaction of the alkenes with XeF2 in CH2Cl2 at room temperature. The linear relationship between log k(rel) and IP with a regression slope of -2.08 and a correlation constant of 0.942, presented for the first time for any fluorination reaction of organic compounds, demonstrates that ct-bond disruption is the rate-determining step in the fluorine addition process for the series of alkenes 1-11. The course of reaction of the series of three 1-phenyl-benzocyclenes (10-12) with XeF2 was investigated. The addition-elimination process, forming 3-phenyl-2-fluoro-1H-indene (15a), was found exclusively in the case of 9-phenyl-1H-indene (12), while the formation of diastereoisomeric pairs of vicinal difluorides (13 and 14), with the trans isomers slightly predominant, was established in the case of 1,2-dihydro-4-phenylnaphthalene (10) and 6,7-dihydro-9-phenyl-5H-benzocycloheptene (11). On heating the vicinal difluorides 13 and 14 HF was released, thus yielding 3-fluoro-4-phenyl-1,2-dihydronaphthalene (15b) and 6,7-dihydro-8-fluoro-9-phenyl-5H-benzocycloheptene (15c), respectively.

  DOI：

  10.1021/jo00099a015

文献信息

• Evidence for the existence of methyl hypofluorite: methanolysis of xenon difluoride
  作者：Dale F. Shellhamer、Carol M. Curtis、Don R. Hollingsworth、Mark L. Ragains、Ruthann E. Richardson、Victor L. Heasley、Gene E. Heasley

  DOI：10.1016/s0040-4039(00)87287-1

  日期：——

  Methyl hypofluorite is indicated as an intermediate in the reaction of xenon difluoride with alkenes in methanol as solvent.

  次氟甲烷指示为在甲醇作为溶剂的二氟化氙与烯烃反应中的中间体。
• Regioselective chemistry of methoxyxenon fluoride
  作者：Dale F. Shellhamer、Carl M. Curtis、Robert H. Dunham、Don R. Hollingsworth、Mark L. Ragains、Ruthann E. Richardson、Victor L. Heasley、Scott A. Shackelford、Gene E. Heasley

  DOI：10.1021/jo00215a032

  日期：1985.7
• SHELLHAMER, D. F.;CURTIS, C. M.;HOLLINGSWORTH, D. R.;RAGAINS, M. L.;RICHA+, TETRAHEDRON LETT., 1982, 23, N 21, 2157-2160
  作者：SHELLHAMER, D. F.、CURTIS, C. M.、HOLLINGSWORTH, D. R.、RAGAINS, M. L.、RICHA+

  DOI：——

  日期：——
• JPH024755A
  申请人：——

  公开号：JPH024755A

  公开（公告）日：1990-01-09
• Fluorination with XeF2. Part 40. The Important Role of .pi.-Bond Disruption in Fluorine Addition to Phenyl-Substituted Alkenes
  作者：Stojan Stavber、Tjasa Sotler、Marko Zupan、Arkadij Popovic

  DOI：10.1021/jo00099a015

  日期：1994.10

  Ionization potentials (IP) for 11 mono- and alpha,alpha-diphenyl-substituted acyclic and cyclic alkenes 1-11 were measured under the same conditions, using a mass spectrometric technique and applying electron impact ionization. The values, ranging from 8.68 eV for styrene (1) to as low as 7.67 eV for 1,2-dihydro-4-phenylnaphthalene (10), were correlated with the logarithms of the relative rates (k(rel), relative to 1,1-diphenylethene) of fluorine addition across the carbon-carbon double bond in HF-catalyzed reaction of the alkenes with XeF2 in CH2Cl2 at room temperature. The linear relationship between log k(rel) and IP with a regression slope of -2.08 and a correlation constant of 0.942, presented for the first time for any fluorination reaction of organic compounds, demonstrates that ct-bond disruption is the rate-determining step in the fluorine addition process for the series of alkenes 1-11. The course of reaction of the series of three 1-phenyl-benzocyclenes (10-12) with XeF2 was investigated. The addition-elimination process, forming 3-phenyl-2-fluoro-1H-indene (15a), was found exclusively in the case of 9-phenyl-1H-indene (12), while the formation of diastereoisomeric pairs of vicinal difluorides (13 and 14), with the trans isomers slightly predominant, was established in the case of 1,2-dihydro-4-phenylnaphthalene (10) and 6,7-dihydro-9-phenyl-5H-benzocycloheptene (11). On heating the vicinal difluorides 13 and 14 HF was released, thus yielding 3-fluoro-4-phenyl-1,2-dihydronaphthalene (15b) and 6,7-dihydro-8-fluoro-9-phenyl-5H-benzocycloheptene (15c), respectively.