(Z/E)-1,2-difluoro-1-iodoethene

• 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: (Z/E)-1,2-difluoro-1-iodoethene
• 英文别名: 1,2-difluoro-1-iodoethene
• 化学式: C₂HF₂I
• 分子量: 189.931
• InChiKey: FEJGXYOLCAYRJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z/E)-1,2-difluoro-1-iodoethene 在 正丁基锂 作用下， 以 四氢呋喃 、 氘代四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 生成 (E)-difluoroethenyllithium
  参考文献：
  名称：

  1-氟-1-硫代乙烯的低温19 F NMR光谱：稳定性，位移和意外的耦合常数

  摘要：

  已经通过低温19 F NMR光谱测定了在β位置带有氢，氟，苯基和/或二甲基苯基甲硅烷基的稳定化的1-氟-1-硫代乙烯的半衰期和氟原子位移。一些1-氟-1- lithioethenes显示的异常低的值的反式- 3 Ĵ FF偶合常数。讨论了类胡萝卜素形成的立体选择性以及构型对稳定性的影响。

  DOI：

  10.1016/s0022-1139(01)00553-x
• 作为产物：
  描述：

  (Z/E)-1,2-difluoro-1-(triethylsilyl)ethylene 在 potassium fluoride 、 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 36.0h， 生成 (Z/E)-1,2-difluoro-1-iodoethene
  参考文献：
  名称：

  Stereoselective Preparation of (Z)-α,β-Difluorostyrenes and Stereospecific Conversion to (E)-α,β-Difluoro-β-iodostyrenes¹

  摘要：

  Substituted aromatic iodides coupled with (E)-HFC=CFZnI: (E:Z 95:5) under mild conditions, in the presence of catalytic Pd(PPh3)(4) in DMF to give (Z)-alpha,beta-difluorostyrenes in good yields. The coupling reaction was tolerant of a variety of functionalities. Isomerically pure (Z)-alpha,beta-difluorostyrenes were readily converted to the corresponding (E)-alpha,beta-difluoro-beta-iodostyrenes in good yields by two methods; in one method, treatment of the (Z)-alpha,beta-difluorostyrenes with LTMP at low-temperature gave vinyllithium reagents which were captured in situ with Bu3SnCl to form vinylstannanes. The intermediate vinylstannanes could be isolated or treated directly with I-2 to give (E)-alpha,beta-difluoro-beta-iodostyrenes in a one-flask procedure. In a second approach, n-BuLi was utilized to pregenerate vinyllithium reagents which were quenched with I-2 to afford (E)-alpha,beta-difluoro-beta-iodostyrenes.

  DOI：

  10.1021/jo971434o

文献信息

• Stereoselective preparation of (Z)-α,β-difluorostyrenes
  作者：Charles R. Davis、Donald J. Burton

  DOI：10.1016/0040-4039(96)01628-0

  日期：1996.9

  Substituted aromatic iodides couple with (E)-HFCCFZnI, under mild conditions, in the presence of catalytic Pd(PPh3)4 in DMF to give the title compounds in good yield.

  在温和的条件下，在DMF中催化的Pd（PPh 3）4存在下，取代的芳族碘化物与（E）-HFCCFZnI偶联，以高收率得到标题化合物。
• Low-temperature 19F NMR spectroscopy of 1-fluoro-1-lithioethenes
  作者：Jaroslav Kvı́čala、Richard Hrabal、Jiřı́ Czernek、Ivana Bartošová、Oldřich Paleta、Andrew Pelter

  DOI：10.1016/s0022-1139(01)00553-x

  日期：2002.2

  1-fluoro-1-lithioethenes bearing hydrogen, fluorine, phenyl, and/or dimethylphenylsilyl groups in the β-positions have been determined by a low-temperature 19F NMR spectroscopy. Some 1-fluoro-1-lithioethenes displayed an exceptionally low value of the trans-3JFF coupling constant. Stereoselectivity of carbenoid formation, as well as an effect of configuration on the stability is discussed.

  已经通过低温19 F NMR光谱测定了在β位置带有氢，氟，苯基和/或二甲基苯基甲硅烷基的稳定化的1-氟-1-硫代乙烯的半衰期和氟原子位移。一些1-氟-1- lithioethenes显示的异常低的值的反式- 3 Ĵ FF偶合常数。讨论了类胡萝卜素形成的立体选择性以及构型对稳定性的影响。
• Stereoselective Preparation of (<i>Z</i>)-α,β-Difluorostyrenes and Stereospecific Conversion to (<i>E</i>)-α,β-Difluoro-β-iodostyrenes¹
  作者：Charles R. Davis、Donald J. Burton

  DOI：10.1021/jo971434o

  日期：1997.12.1

  Substituted aromatic iodides coupled with (E)-HFC=CFZnI: (E:Z 95:5) under mild conditions, in the presence of catalytic Pd(PPh3)(4) in DMF to give (Z)-alpha,beta-difluorostyrenes in good yields. The coupling reaction was tolerant of a variety of functionalities. Isomerically pure (Z)-alpha,beta-difluorostyrenes were readily converted to the corresponding (E)-alpha,beta-difluoro-beta-iodostyrenes in good yields by two methods; in one method, treatment of the (Z)-alpha,beta-difluorostyrenes with LTMP at low-temperature gave vinyllithium reagents which were captured in situ with Bu3SnCl to form vinylstannanes. The intermediate vinylstannanes could be isolated or treated directly with I-2 to give (E)-alpha,beta-difluoro-beta-iodostyrenes in a one-flask procedure. In a second approach, n-BuLi was utilized to pregenerate vinyllithium reagents which were quenched with I-2 to afford (E)-alpha,beta-difluoro-beta-iodostyrenes.