1-tert-butyl-3,3-diphenyl-thioallene episulfide | 111278-37-6

• 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: 1-tert-butyl-3,3-diphenyl-thioallene episulfide
• 英文别名: 2-Benzhydrylidene-3-tert-butylthiirane
• CAS: 111278-37-6
• 化学式: C₁₉H₂₀S
• 分子量: 280.434
• InChiKey: AASXXWFHJDWZBW-UHFFFAOYSA-N

物化性质

• 沸点：
  405.4±45.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-tert-butyl-3,3-diphenyl-thioallene episulfide 在 三氟乙酸 作用下， 生成 1-tert-Butyl-3-phenyl-1H-indene-2-thiol
  参考文献：
  名称：

  烯丙基硫醚的异构化和脱硫

  摘要：

  不均匀取代的烯丙硫醚进行了热和酸催化的异构化和脱硫，这通过互变异构体再循环和硫氧基烯丙基中间体的硫消除而得以合理化。

  DOI：

  10.1016/s0040-4039(00)95422-4
• 作为产物：
  描述：

  3-[2,2-Dimethyl-prop-(Z)-ylidene]-2,2-diphenyl-thiirane 在 silica gel 作用下， 生成 1-tert-butyl-3,3-diphenyl-thioallene episulfide
  参考文献：
  名称：

  烯丙基硫醚的异构化和脱硫

  摘要：

  不均匀取代的烯丙硫醚进行了热和酸催化的异构化和脱硫，这通过互变异构体再循环和硫氧基烯丙基中间体的硫消除而得以合理化。

  DOI：

  10.1016/s0040-4039(00)95422-4

文献信息

• Palladium(0)-catalyzed intra- and intermolecular cyclization reactions of allene episulfides
  作者：Nami Choi、Yoshio Kabe、Wataru Ando

  DOI：10.1016/0040-4039(91)80042-5

  日期：1991.1

  Palladium(0) catalyzed reaction of allene episulfide with DMAD yielded sulfur containing medium ring compounds. Allyl substituted allene episulfide afforded an intramolecular cyclization product, [2.1.1] thiahexane derivative via η3-thioallyl complex.

  钯（0）催化的烯丙基环硫与DMAD的反应生成了含硫的中环化合物。烯丙基取代的环硫丙二烯，得到的分子内环化产物，经由η[2.1.1] thiahexane衍生物3 -thioallyl复杂。
• Ando, Wataru; Choi, Nami; Kabe, Yoshio, Journal of the American Chemical Society, 1990, vol. 112, # 11, p. 4574 - 4576
  作者：Ando, Wataru、Choi, Nami、Kabe, Yoshio

  DOI：——

  日期：——
• Formation of thioruthenium carbonyl clusters via a thioallyl cation complex
  作者：Nami Choi、Yoshio Kabe、Wataru Ando

  DOI：10.1021/om00038a018

  日期：1992.2

  Tetramethylallene episulfide (1a) reacts with Ru3(CO)12 to afford the oxidative addition hydride clusters Ru3(CO)10[mu-S(C = CMe2)C(Me2) = CH2](mu-H) (2) and Ru3(CO)9[mu-S(C = CMe2)C(Me = CH2](mu-H) (3), respectively. The structure of 2 was characterized crystallographically. The cluster 2 undergoes decarbonylation at 60-degrees-C to form 3 in 47% yield. The cluster 3 can regenerate 2 by bubbling with carbon monoxide under 1 atm of pressure at room temperature, in 80% yield. The chemical correlations leave little doubt about the structure of 3 which has a six-electron donating (mu-S)(mu-H)-eta(2)-dimethylpentadine ligand. The reaction of 1-tert-butyl-3,3-diphenylallene 1-episulfide (1b) with Ru3(CO)12 resulted in the formation of the cluster Ru3(CO)10[2-(mu-S)-1-tert-butyl-3-phenylindene](mu-H) (5). The X-ray structure of 5 shows that intramolecular cyclization has occurred besides C-S bond cleavage. The thioallyl cation complexes 9 and 10 are the intermediates of the formation of clusters 2 and 5. Upon warming to 80-120-degrees-C, 2 and 5 were finally converted to desulfurized products 2,4-dimethyl-1,3-pentadiene (6) (quantitative) and 1-tert-butyl-3-phenylindene (7) (56%) along with thio cluster HRu5(CO)15[2-(mu-S)-1-tert-butyl-3-phenylindene](mu-4-S) (8) (30%).
• (Thioallyl)iron tricarbonyl complexes
  作者：Nami Choi、Yoshio Kabe、Wataru Ando

  DOI：10.1021/om00040a021

  日期：1992.4

  The tetramethylallene episulfide 1a reacts with Fe2(CO)9 to afford (tetramethylthioallyl)iron tricarbonyl complex 2a and (mu-2,4-dimethyl-2-pentene-3,4-dithiolato-kappa(2)S:kappa(2)S')diiron hexacarbonyl (3). The structure of 3 was characterized crystallographically. The reaction of 1-tert-butyl-3,3-diphenylallene 1-episulfide (1b) with Fe2(CO)9 resulted in the formation of (1-tert-butyl-3,3-diphenyl-2-thioallyl)iron tricarbonyl (2b). The (thioallyl)iron tricarbonyl complex 2b exists as an eta(4)-pi-complex as revealed by H-1 and C-13 NMR spectroscopy as well as by X-ray diffraction analysis. Thermolysis of 2b in the presence of carbon monoxide gave 2-tert-butyl-4-(diphenylmethylidene)thietan-3-one (7). Complex 2b reacts with PPh3 to give 7 and metalathiopentanone 8. Heating of 8 gave 7 and a corresponding allene 5b. According to the structure of 7 and 8 and chemical observations, thermolysis of 8 took place to give 7 via a metathesis-like reaction of 1,2- or 1,3-metalathietane 13 and 15.