[1-(phenylthio)methylene-3-mesityl]imidazolium bromide | 1386412-27-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: [1-(phenylthio)methylene-3-mesityl]imidazolium bromide
• CAS: 1386412-27-6
• 化学式: Br*C₁₉H₂₁N₂S
• 分子量: 389.359
• InChiKey: JYGSYXSCFHKITQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  8.81
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  [1-(phenylthio)methylene-3-mesityl]imidazolium bromide 以 二氯甲烷 、 二氯甲烷-D2 为溶剂， 生成 ([1-(phenylthio)methylene-3-mesityl]imidazolyl-2-ene)palladium(0)(η2-maleic anhydride)(η2-dimethyl-2-butynedioate)
  参考文献：
  名称：

  The interaction between heteroditopic pyridine–nitrogen NHC with novel sulfur NHC ligands in palladium(0) derivatives: Synthesis and structural characterization of a bis-carbene palladium(0) olefin complex and formation in solution of an alkene–alkyne mixed intermediate as a consequence of the ligands hemilability

  摘要：

  We have synthesized a new class of heteroditopic chelating ligands bearing the phenylthiomethyl group and variously substituted imidazole derivatives and the corresponding complexes [Pd(eta(2)-ma)(R-NHC-CH2-SPh) (ma = maleic anhydride; R = methyl, mesityl, di-i-propylphenyl). We have compared their chemical characteristics and reactivity with those of similar palladium(0) complexes bearing the R-NHC-CH2-Py ligands.The hemilability of the above-mentioned moieties is apparent when their palladium derivatives react with an excess of the same or different heteroditopic ligands. In these cases, we obtained complexes bearing maleic anhydride and two mono-coordinated heteroditopic ligands bound to the same metal center. However, at variance with the generally accepted opinion, precipitation of AgBr does not warrant the quantitative formation of the bis-heteroditopic Pd(0) derivative and in some cases, a reaction involving a heterogeneous equilibrium is observed.The reaction of the palladium(0) carbene-sulfur or carbene-nitrogen complexes with the alkyne dimethyl-2-butynedioate (dmbd) to give palladacyclometallate derivatives is not always warranted and formation of the intermediate [Pd(eta(2)-ma)(eta(2)-dmdb)(kappa(1)-Mes-NHC-CH2-SPh)] is detected only in one case.Finally, we have carried out a diffractometric study on the solid-state structures of two derivatives and in particular we describe the configurations of the complex [Pd(eta(2)-ma)(kappa(1)-Me-NHC-CH2-SPh)(2)] and of [Pd(eta(2)-ma)(Me-NHC-CH2-SPh)]. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.04.018
• 作为产物：
  描述：

  氯甲基苯硫醚 、 1-(2,4,6-三甲基苯基)-咪唑 在 potassium bromide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 [1-(phenylthio)methylene-3-mesityl]imidazolium bromide
  参考文献：
  名称：

  合成带有异位NHC-S配体的新型钯烯丙基配合物。双卡宾钯烯丙基配合物之间卡宾交换的动力学研究

  摘要：

  我们已经合成了几种新颖的钯烯丙基和1,1-二甲基烯丙基配合物，它们带有不同的异位NHC-S配体，形成了一个带有金属中心的五元螯合环。我们能够利用硫醚硫的半合成能力合成一些均化的双卡宾烯丙基衍生物。在制备混合尝试双（-carbene络合物带有两个不同heteroditopic卡宾即- S和NHC - PY NHC）同时配位到钯中心导致卡宾转移金属化与两个纯均配型的和的统计分布的平衡混合物的形成混在一起-卡宾钯烯丙基络合物的溶液。在两种不同的情况下，测量了平衡反应的速率并提供了机械学假设。最后，我们确定了仅带有一种NHC-S异位碳烯和双碳烯（NHC-S，NHC-Py）钯烯丙基衍生物的配合物的固态结构。

  DOI：

  10.1016/j.jorganchem.2013.01.016