α-(3-Methoxyphenyl)-α-(2,3,4,5,6-pentachlorophenyl)acetonitrile

• 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: α-(3-Methoxyphenyl)-α-(2,3,4,5,6-pentachlorophenyl)acetonitrile
• 英文别名: 2-(3-Methoxyphenyl)-2-(2,3,4,5,6-pentachlorophenyl)acetonitrile
• 化学式: C₁₅H₈Cl₅NO
• 分子量: 395.5
• InChiKey: NWEAEYVTSACIFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-甲氧基苯乙腈 、 六氯苯 在 正丁基锂 作用下， 以 乙醚 为溶剂， 以92%的产率得到α-(3-Methoxyphenyl)-α-(2,3,4,5,6-pentachlorophenyl)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

• α-(2,3,5,6-Tetrachlorophenyl)-α-(3-thienyl)acetonitrile and α-(3-Methoxyphenyl)-α-(2,3,4,5,6-pentachlorophenyl)acetonitrile
  作者：H. Zhang、H. M. Refat、E. Biehl

  DOI：10.1107/s0108270195004288

  日期：1995.8.15

  The C-Cl distances of the tetrachlorophenyl moiety in alpha-(2,3,5, 6-tetrachlorophenyl)-alpha-(3-thienyl)acetonitrile, (1), C12H5Cl4NS, are in the range 1.713(3)-1.720(3)Angstrom, and those of the pentachlorophenyl moiety in alpha-(3-methoxyphenyl)-alpha-(2,3,4,5,6-pentachloro phenyl)acetonitrile, (2), C15H8Cl5NO, are in the range 1.695 (9)-1.734 (8) Angstrom. The thienyl ring of compound (1) is almost planar and the dihedral angle between the phenyl and thienyl rings is 78.8 (1)degrees, while that between the two phenyl planes of compound (2) is 88.6(3)degrees.
• 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.