4-Bromo-3-iodobenzenethiol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 英文名称: 4-Bromo-3-iodobenzenethiol
• 英文别名: 4-bromo-3-iodobenzenethiol
• 化学式: C₆H₄BrIS
• 分子量: 314.972
• InChiKey: UWNWKYVIYUOOJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-Bromo-3-iodobenzenethiol 在 aluminum (III) chloride 、 copper(l) iodide 、 bis(acetonitrile)palladium(II) chloride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 4-(5-(tert-butylthio)-2-((triisopropylsilyl)ethynyl)phenyl)-2-methylbut-3-yn-2-ol
  参考文献：
  名称：

  Deltoid versus Rhomboid: Controlling the Shape of Bis-ferrocene Macrocycles by the Bulkiness of the Substituents

  摘要：

  Precise structural control of heteroannularly disubstituted ferrocene (Fc) structures is very challenging as the high rotational mobility of the Fc unit allows a large conformational diversity. Herein we present the syntheses, characterization, and electrochemical investigation of two complementary bis-ferrocene macrocycles, built up via Sonogashira cross coupling and intramolecular ring-closing reaction. While the X-ray structure of 1,2-ethynylbenzene bridged bis-ferrocene complex 1 shows a deltoidal conformation, a stretched oriented rhomboidal bis-ferrocene metalla-cycle 2 is formed when the peripheral benzene rings are decorated with bulky tert-butylsulfanyl groups. VT-NMR spectroscopy is used to assign the rotation of the embedded Fc units in rhomboid 2. Moreover, cyclic voltammetry (CV) of deltoid 1 and rhomboid 2 indicate that electronic communication between both ferrocenyl groups can be neglected, while the electrostatic through space coupling is significant.

  DOI：

  10.1021/acs.organomet.6b00909
• 作为产物：
  描述：

  1-bromo-2-iodo-4-thiocyanatobenzene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 4-Bromo-3-iodobenzenethiol
  参考文献：
  名称：

  Deltoid versus Rhomboid: Controlling the Shape of Bis-ferrocene Macrocycles by the Bulkiness of the Substituents

  摘要：

  Precise structural control of heteroannularly disubstituted ferrocene (Fc) structures is very challenging as the high rotational mobility of the Fc unit allows a large conformational diversity. Herein we present the syntheses, characterization, and electrochemical investigation of two complementary bis-ferrocene macrocycles, built up via Sonogashira cross coupling and intramolecular ring-closing reaction. While the X-ray structure of 1,2-ethynylbenzene bridged bis-ferrocene complex 1 shows a deltoidal conformation, a stretched oriented rhomboidal bis-ferrocene metalla-cycle 2 is formed when the peripheral benzene rings are decorated with bulky tert-butylsulfanyl groups. VT-NMR spectroscopy is used to assign the rotation of the embedded Fc units in rhomboid 2. Moreover, cyclic voltammetry (CV) of deltoid 1 and rhomboid 2 indicate that electronic communication between both ferrocenyl groups can be neglected, while the electrostatic through space coupling is significant.

  DOI：

  10.1021/acs.organomet.6b00909