2-(Trichloromethyl)-1,3-dithiane | 70063-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: 2-(Trichloromethyl)-1,3-dithiane
• CAS: 70063-60-4
• 化学式: C₅H₇Cl₃S₂
• 分子量: 237.602
• InChiKey: ANCVGMLLLYYAOR-UHFFFAOYSA-N

物化性质

• 沸点：
  307.9±37.0 °C(Predicted)
• 密度：
  1.520±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(Trichloromethyl)-1,3-dithiane 在 正丁基锂 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-(1,3-Benzodithiole-2-ylidene)-1,3-dithiane
  参考文献：
  名称：

  A variable mechanism for the nucleophilic vinylic substitutions in a series of gem-dihalogenated alkenes by a bidentate sulfur nucleophile: an experimental and AM1 theoretical study

  摘要：

  The nucleophilic substitutions of a series of gem-dihalogenated alkenes 3,5,7,8, and 9 (RS)2C=CX2 (X = Cl, F) with 1,2-benzenedithiolate b have been studied. Depending on the structures of the R groups (alkyl, saturated and unsaturated cycloalkyls, aromatic ring), the course of the reactions and the structures of the yielded products are modified. In the frame of the addition-elimination-type mechanism for these nucleophilic substitutions, the energy contents of the anionic intermediates, resulting from the additions of the nucleophile b to the unsaturated centers, is calculated at the AM1 method level. For the compounds 5, 7, 8, and 9, the calculated energies nicely corroborate the experimental results. For 3, anionic intermediates are no longer found by calculation, and a synchronous single-step substitution is strongly suggested.

  DOI：

  10.1021/jo00069a035
• 作为产物：
  描述：

  1,3-丙二硫醇 、 三氯乙醛 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以65%的产率得到2-(Trichloromethyl)-1,3-dithiane
  参考文献：
  名称：

  A variable mechanism for the nucleophilic vinylic substitutions in a series of gem-dihalogenated alkenes by a bidentate sulfur nucleophile: an experimental and AM1 theoretical study

  摘要：

  The nucleophilic substitutions of a series of gem-dihalogenated alkenes 3,5,7,8, and 9 (RS)2C=CX2 (X = Cl, F) with 1,2-benzenedithiolate b have been studied. Depending on the structures of the R groups (alkyl, saturated and unsaturated cycloalkyls, aromatic ring), the course of the reactions and the structures of the yielded products are modified. In the frame of the addition-elimination-type mechanism for these nucleophilic substitutions, the energy contents of the anionic intermediates, resulting from the additions of the nucleophile b to the unsaturated centers, is calculated at the AM1 method level. For the compounds 5, 7, 8, and 9, the calculated energies nicely corroborate the experimental results. For 3, anionic intermediates are no longer found by calculation, and a synchronous single-step substitution is strongly suggested.

  DOI：

  10.1021/jo00069a035

文献信息

• A variable mechanism for the nucleophilic vinylic substitutions in a series of gem-dihalogenated alkenes by a bidentate sulfur nucleophile: an experimental and AM1 theoretical study
  作者：Yves Gimbert、Alec Moradpour、Georges Dive、Dominique Dehareng、Khaled Lahlil

  DOI：10.1021/jo00069a035

  日期：1993.8

  The nucleophilic substitutions of a series of gem-dihalogenated alkenes 3,5,7,8, and 9 (RS)2C=CX2 (X = Cl, F) with 1,2-benzenedithiolate b have been studied. Depending on the structures of the R groups (alkyl, saturated and unsaturated cycloalkyls, aromatic ring), the course of the reactions and the structures of the yielded products are modified. In the frame of the addition-elimination-type mechanism for these nucleophilic substitutions, the energy contents of the anionic intermediates, resulting from the additions of the nucleophile b to the unsaturated centers, is calculated at the AM1 method level. For the compounds 5, 7, 8, and 9, the calculated energies nicely corroborate the experimental results. For 3, anionic intermediates are no longer found by calculation, and a synchronous single-step substitution is strongly suggested.