2-Formyl-3,4,5,6-tetramethylbenzenesulfonyl fluoride

• 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: 2-Formyl-3,4,5,6-tetramethylbenzenesulfonyl fluoride
• 化学式: C₁₁H₁₃FO₃S
• 分子量: 244.287
• InChiKey: BDLBKQMELCKESN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  一氧化碳 、 1,2,3,5-四甲基苯 在 五氟化锑 、 氟磺酸 作用下， 反应 24.0h， 以15%的产率得到2-Formyl-3,4,5,6-tetramethylbenzenesulfonyl fluoride
  参考文献：
  名称：

  Dual Reactivity of the Formyl Cation as an Electrophile and a Broensted Acid in Superacids

  摘要：

  The nature of the formyl cation in the Gattermann-Koch formylation was studied by comparing the formylation with the acetylation and sulfonation in CF3SO3H-SbF5 and FSO3H-SbF5, respectively. The results of the kinetic studies in CF3SO3H-SbF5 showed that the formyl cation has dual reactivity as an electrophile and as a Bronsted acid. Upon comparing the formylation with the sulfonation in FSO3H-SbF5, it was found that the protonated aromatic compounds also act as Bronsted acids to produce formyl cations. Therefore, the formylation has a priority over other typical electrophilic substitutions under conditions where most of aromatic compounds are protonated because the formyl cation is reproduced close to the aromatic compounds by the protonation of CO with not only superacids but also protonated aromatic compounds.

  DOI：

  10.1021/jo00117a041

文献信息

• Dual Reactivity of the Formyl Cation as an Electrophile and a Broensted Acid in Superacids
  作者：Matsuo Tanaka、Masahiro Fujiwara、Hisanori Ando

  DOI：10.1021/jo00117a041

  日期：1995.6

  The nature of the formyl cation in the Gattermann-Koch formylation was studied by comparing the formylation with the acetylation and sulfonation in CF3SO3H-SbF5 and FSO3H-SbF5, respectively. The results of the kinetic studies in CF3SO3H-SbF5 showed that the formyl cation has dual reactivity as an electrophile and as a Bronsted acid. Upon comparing the formylation with the sulfonation in FSO3H-SbF5, it was found that the protonated aromatic compounds also act as Bronsted acids to produce formyl cations. Therefore, the formylation has a priority over other typical electrophilic substitutions under conditions where most of aromatic compounds are protonated because the formyl cation is reproduced close to the aromatic compounds by the protonation of CO with not only superacids but also protonated aromatic compounds.