5,5'-Bis-methylsulfanyl-3,3'-diphenyl-[5,5']bi[[1,4,2]dithiazolyl] | 151451-88-6

• 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: 5,5'-Bis-methylsulfanyl-3,3'-diphenyl-[5,5']bi[[1,4,2]dithiazolyl]
• 英文别名: 5-Methylsulfanyl-5-(5-methylsulfanyl-3-phenyl-1,4,2-dithiazol-5-yl)-3-phenyl-1,4,2-dithiazole
• CAS: 151451-88-6
• 化学式: C₁₈H₁₆N₂S₆
• 分子量: 452.734
• InChiKey: GPYBUOSJWUFPIP-UHFFFAOYSA-N

物化性质

• 沸点：
  627.1±65.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  177
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,5'-Bis-methylsulfanyl-3,3'-diphenyl-[5,5']bi[[1,4,2]dithiazolyl] 在 溴 、 碘 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-3,3'-Diphenyl-[5,5']bi[[1,4,2]dithiazolylidene]
  参考文献：
  名称：

  Synthesis and Properties of Tetrathiadiazafulvalenes [RCNS2C:CS2NCR] (R = H, Me, Ph)

  摘要：

  Reduction of 5-(methylthio)-1,4,2-dithiazolium (3, R = H, Me, Ph) salts with zinc powder yields the corresponding diazahexathioorthooxalate derivatives (RCNS(2))(MeS)CC(SMe)(S(2)NCR) (4, R = H, Me, Ph). Thermolysis of these materials in the presence of catalytic quantities of iodine affords the tetrathiadiazafulvalenes [RCNS(2)C=CS(2)NCR] (2, R = H, Me, Ph) in good yield. Separation of the cis and trans isomers can be achieved with relative ease for the R = Me and Ph derivatives, but co-crystallization occurs for the two isomers of the R = H compound. Tetrathiadiazafulvalenes are poorer electron donors than TTF; cyclic voltammetry nonetheless reveals two reversible oxidation processes. The ESR spectrum of the radical cation trans-2(+.) (R = Ph) consists of a quintet with a(N) = 0.08 mT, g = 2.0071.

  DOI：

  10.1021/jo00090a016
• 作为产物：
  描述：

  5-methylthio-3-phenyl-1,4,2-dithiazolium tetrafluoroborate 在 锌 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以100%的产率得到5,5'-Bis-methylsulfanyl-3,3'-diphenyl-[5,5']bi[[1,4,2]dithiazolyl]
  参考文献：
  名称：

  Synthesis and Properties of Tetrathiadiazafulvalenes [RCNS2C:CS2NCR] (R = H, Me, Ph)

  摘要：

  Reduction of 5-(methylthio)-1,4,2-dithiazolium (3, R = H, Me, Ph) salts with zinc powder yields the corresponding diazahexathioorthooxalate derivatives (RCNS(2))(MeS)CC(SMe)(S(2)NCR) (4, R = H, Me, Ph). Thermolysis of these materials in the presence of catalytic quantities of iodine affords the tetrathiadiazafulvalenes [RCNS(2)C=CS(2)NCR] (2, R = H, Me, Ph) in good yield. Separation of the cis and trans isomers can be achieved with relative ease for the R = Me and Ph derivatives, but co-crystallization occurs for the two isomers of the R = H compound. Tetrathiadiazafulvalenes are poorer electron donors than TTF; cyclic voltammetry nonetheless reveals two reversible oxidation processes. The ESR spectrum of the radical cation trans-2(+.) (R = Ph) consists of a quintet with a(N) = 0.08 mT, g = 2.0071.

  DOI：

  10.1021/jo00090a016

文献信息

• Tetrathiadiazafulvalenes; preparation and characterisation of cis- and trans-[RCNS₂CCS₂NCR](R = Me, Ph)
  作者：Richard T. Oakley、John F. Richardson、Rupert E. V. H. Spence

  DOI：10.1039/c39930001226

  日期：——

  Tetrathiadiazafulvalenes can be prepared by the reductive coupling of 5-methylthio-1,4,2-dithiazolium salts, and thermolysis of the resulting hexathiooxalates; oxidation of tetrathiadiazafulvalenes affords the corresponding radical cations.