trans-1,2-Dicyano-1,2-di-(3-thienyl)ethylene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: trans-1,2-Dicyano-1,2-di-(3-thienyl)ethylene
• 英文别名: (E)-2,3-di(thiophen-3-yl)but-2-enedinitrile
• 化学式: C₁₂H₆N₂S₂
• 分子量: 242.325
• InChiKey: GRWSSLFNDZYKHX-VAWYXSNFSA-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：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-噻吩乙腈 在 正丁基锂 、 pentachlorophenyllithium 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以56%的产率得到α-(3-Thiophene-yl)-α-(2,3,5,6-tetrachlorophenyl)acetonitrile
  参考文献：
  名称：

  Reaction of Hexachlorobenzene and (Pentachlorophenyl)lithium with .alpha.-Arylacetonitriles

  摘要：

  (Pentachlorophenyl)lithium (2) reacts with alpha-lithio-alpha-arylacetonitriles (4) at -70 degrees C to room temperature to supply alpha-aryl-alpha-(2,3,5,6-tetrachlorophenyl)ace a. Small amounts of 1,2,4,5-tetrachlorobenzene (8) and trans-1,2-dicyano-1,2-diarylethylenes 9 are also obtained; however, no alpha-tetrachloroarylated nitriles 6 from 3,4,5,6-tetrachlorobenzyne were detected. Similar treatment of hexachlorobenzene (1) and 4 afforded alpha-aryl-alpha-(2,3,4,5,6-pentachlorophenyl)acetonitriles 10. The addition of 2 to 4 at tetrachlorobenzyne-generating temperatures (0-20 degrees C) gave a complex mixture containing mainly dimeric and polymeric materials; 6 was not found. A mechanism is proposed for the reaction of 2 and 4 which suggests that nitriles 7 are formed by the condensation of 2 and 4 via a four-centered transition state and that alkenes 9 are supplied by a base-mediated dimerization of alpha-chloro-alpha-arylacetonitriles 13, formed by a lithium-chlorine exchange between 2 and 4. Nitriles 10 most likely are provided from the reaction of 1 and 4 by the usual aromatic nucleophilic substitution pathway.

  DOI：

  10.1021/jo00112a019

文献信息

• Reaction of Hexachlorobenzene and (Pentachlorophenyl)lithium with .alpha.-Arylacetonitriles
  作者：Hala Mohammed Refat、John Waggenspack、Mahesh Dutt、Hongming Zhang、A. A. Fadda、Ed Biehl

  DOI：10.1021/jo00112a019

  日期：1995.4

  (Pentachlorophenyl)lithium (2) reacts with alpha-lithio-alpha-arylacetonitriles (4) at -70 degrees C to room temperature to supply alpha-aryl-alpha-(2,3,5,6-tetrachlorophenyl)ace a. Small amounts of 1,2,4,5-tetrachlorobenzene (8) and trans-1,2-dicyano-1,2-diarylethylenes 9 are also obtained; however, no alpha-tetrachloroarylated nitriles 6 from 3,4,5,6-tetrachlorobenzyne were detected. Similar treatment of hexachlorobenzene (1) and 4 afforded alpha-aryl-alpha-(2,3,4,5,6-pentachlorophenyl)acetonitriles 10. The addition of 2 to 4 at tetrachlorobenzyne-generating temperatures (0-20 degrees C) gave a complex mixture containing mainly dimeric and polymeric materials; 6 was not found. A mechanism is proposed for the reaction of 2 and 4 which suggests that nitriles 7 are formed by the condensation of 2 and 4 via a four-centered transition state and that alkenes 9 are supplied by a base-mediated dimerization of alpha-chloro-alpha-arylacetonitriles 13, formed by a lithium-chlorine exchange between 2 and 4. Nitriles 10 most likely are provided from the reaction of 1 and 4 by the usual aromatic nucleophilic substitution pathway.