2,3-dichloro-6-methoxyphenyllithium | 1017576-41-8

• 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: 2,3-dichloro-6-methoxyphenyllithium
• CAS: 1017576-41-8
• 化学式: C₇H₅Cl₂LiO
• 分子量: 182.963
• InChiKey: RCLZSOLRRBFPEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-dichloro-6-methoxyphenyllithium 以 四氢呋喃 、 甲苯 为溶剂， 生成 6-chloro-3-methoxybenzyne
  参考文献：
  名称：

  Structural and Rate Studies of the Formation of Substituted Benzynes

  摘要：

  The key elimination step for the formation of 3-substituted and 3,6-disubstituted benzynes from 2-haloaryllithiums displays a pronounced solvent-dependent regioselectivity. All 2-haloaryllithiums with electron withdrawing groups in the 6 position are shown by Li-6 and C-13 NMR spectroscopic studies to be monomers in THF. DFT computational studies implicate trisolvates. Rate studies reveal that LiF eliminates via monomer-based pathways requiring THF dissociation whereas LiCl eliminates via nondissociative pathways. Elimination to form 3-chloro- and 3-fluorobenzyne from 2-chloro-6-fluorophenyllithium displays a pronounced solvent-dependent regioselectivity that is traced to competing solvent-dissociative and nondissociative dissociative pathways for the elimination of LiCl and LiF, respectively.

  DOI：

  10.1021/ja0754655

文献信息

• Structural and Rate Studies of the Formation of Substituted Benzynes
  作者：Jason C. Riggs、Antonio Ramirez、Matthew E. Cremeens、Crystal G. Bashore、John Candler、Michael C. Wirtz、Jotham W. Coe、David B. Collum

  DOI：10.1021/ja0754655

  日期：2008.3.1

  The key elimination step for the formation of 3-substituted and 3,6-disubstituted benzynes from 2-haloaryllithiums displays a pronounced solvent-dependent regioselectivity. All 2-haloaryllithiums with electron withdrawing groups in the 6 position are shown by Li-6 and C-13 NMR spectroscopic studies to be monomers in THF. DFT computational studies implicate trisolvates. Rate studies reveal that LiF eliminates via monomer-based pathways requiring THF dissociation whereas LiCl eliminates via nondissociative pathways. Elimination to form 3-chloro- and 3-fluorobenzyne from 2-chloro-6-fluorophenyllithium displays a pronounced solvent-dependent regioselectivity that is traced to competing solvent-dissociative and nondissociative dissociative pathways for the elimination of LiCl and LiF, respectively.