1,9-Bis(phenylseleno)dibenzothiophene | 158637-46-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 1,9-Bis(phenylseleno)dibenzothiophene
• 英文别名: 1,9-Bis(phenylselanyl)dibenzothiophene
• CAS: 158637-46-8
• 化学式: C₂₄H₁₆SSe₂
• 分子量: 494.377
• InChiKey: PMACTNPMANPNHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,9-Bis(phenylseleno)dibenzothiophene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以71%的产率得到1-(Phenylseleninyl)-9-(phenylseleno)dibenzothiophene
  参考文献：
  名称：

  Effect of Through-Space Interaction on the Photolytic Desulfurization or Deselenization and Intramolecular Cyclization Reactions of 1,9-Disubstituted Dibenzochalcogenophenes

  摘要：

  1,9-Dithia and 1,9-diselena substituents in dibenzochalcogenophenes 1 are in close proximity within the van der Waals S-S and Se-Se contacts and hence have a strong through-space interaction. Photolysis of the compounds 1 with a 400 W high-pressure mercury lamp in benzene produces triphenyleno[4,5-bcd]chalcogenophenes 2 and tribenzo[bc,e,hi][2,7]dichalcogenaazulenes 3 in high yields, except for the dibenzofuran derivative, via photoexcitation, sequential desulfurization or deselenization, and intramolecular cyclization. In the reaction, 1,9-bis(phenylthio)dibenzofuran (1e) exhibits lower reactivity as compared with other dibenzothiophene and dibenzoselenophene derivatives. The X-ray crystallographic analysis of 1,9-bis(phenylseleno)dibenzoselenaphene (1a), 1,9-bis(phenylseleno)dibenzothiophene (1b), and 1,9-bis(phenylthio)dibenzoselenophene (1c) demonstrated that; their structures are distorted as is also that of 1,9-bis(phenylthio)dibenzothiophene (1d),(1) while dibenzofuran derivative 1e was found to be a nearly planar molecule. The structure and reactivity relationship of compounds 1a-e was examined in the photolytic reactions by comparing their interheteroatomic distances at the 1,9 positions and their oxidation potentials. Furthermore, compounds 1a-e afforded the corresponding monosulfoxides and bis-sulfoxides on oxidation with m-chloroperbenzoic acid which were photolyzed readily to give also 2 and 3.

  DOI：

  10.1021/jo00102a043
• 作为产物：
  描述：

  4,6-Bis(phenylseleno)thianthrene 5-oxide 在 苯基溴化镁 、 copper dichloride 作用下， 生成 1,9-Bis(phenylseleno)dibenzothiophene
  参考文献：
  名称：

  Effect of Through-Space Interaction on the Photolytic Desulfurization or Deselenization and Intramolecular Cyclization Reactions of 1,9-Disubstituted Dibenzochalcogenophenes

  摘要：

  1,9-Dithia and 1,9-diselena substituents in dibenzochalcogenophenes 1 are in close proximity within the van der Waals S-S and Se-Se contacts and hence have a strong through-space interaction. Photolysis of the compounds 1 with a 400 W high-pressure mercury lamp in benzene produces triphenyleno[4,5-bcd]chalcogenophenes 2 and tribenzo[bc,e,hi][2,7]dichalcogenaazulenes 3 in high yields, except for the dibenzofuran derivative, via photoexcitation, sequential desulfurization or deselenization, and intramolecular cyclization. In the reaction, 1,9-bis(phenylthio)dibenzofuran (1e) exhibits lower reactivity as compared with other dibenzothiophene and dibenzoselenophene derivatives. The X-ray crystallographic analysis of 1,9-bis(phenylseleno)dibenzoselenaphene (1a), 1,9-bis(phenylseleno)dibenzothiophene (1b), and 1,9-bis(phenylthio)dibenzoselenophene (1c) demonstrated that; their structures are distorted as is also that of 1,9-bis(phenylthio)dibenzothiophene (1d),(1) while dibenzofuran derivative 1e was found to be a nearly planar molecule. The structure and reactivity relationship of compounds 1a-e was examined in the photolytic reactions by comparing their interheteroatomic distances at the 1,9 positions and their oxidation potentials. Furthermore, compounds 1a-e afforded the corresponding monosulfoxides and bis-sulfoxides on oxidation with m-chloroperbenzoic acid which were photolyzed readily to give also 2 and 3.

  DOI：

  10.1021/jo00102a043

文献信息

• Effect of Through-Space Interaction on the Photolytic Desulfurization or Deselenization and Intramolecular Cyclization Reactions of 1,9-Disubstituted Dibenzochalcogenophenes
  作者：Takeshi Kimura、Yasuhiro Ishikawa、Kensaku Ueki、Yoji Horie、Naomichi Furukawa

  DOI：10.1021/jo00102a043

  日期：1994.11

  1,9-Dithia and 1,9-diselena substituents in dibenzochalcogenophenes 1 are in close proximity within the van der Waals S-S and Se-Se contacts and hence have a strong through-space interaction. Photolysis of the compounds 1 with a 400 W high-pressure mercury lamp in benzene produces triphenyleno[4,5-bcd]chalcogenophenes 2 and tribenzo[bc,e,hi][2,7]dichalcogenaazulenes 3 in high yields, except for the dibenzofuran derivative, via photoexcitation, sequential desulfurization or deselenization, and intramolecular cyclization. In the reaction, 1,9-bis(phenylthio)dibenzofuran (1e) exhibits lower reactivity as compared with other dibenzothiophene and dibenzoselenophene derivatives. The X-ray crystallographic analysis of 1,9-bis(phenylseleno)dibenzoselenaphene (1a), 1,9-bis(phenylseleno)dibenzothiophene (1b), and 1,9-bis(phenylthio)dibenzoselenophene (1c) demonstrated that; their structures are distorted as is also that of 1,9-bis(phenylthio)dibenzothiophene (1d),(1) while dibenzofuran derivative 1e was found to be a nearly planar molecule. The structure and reactivity relationship of compounds 1a-e was examined in the photolytic reactions by comparing their interheteroatomic distances at the 1,9 positions and their oxidation potentials. Furthermore, compounds 1a-e afforded the corresponding monosulfoxides and bis-sulfoxides on oxidation with m-chloroperbenzoic acid which were photolyzed readily to give also 2 and 3.