diphenyl(phenylthio)bismuthane | 115419-47-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: diphenyl(phenylthio)bismuthane
• 英文别名: diphenyl(phenylthio)bismuthine；Diphenyl(phenylthio)bismutan；diphenyl bismuth (1+); thiophenolate；Diphenyl-wismut(1+); Thiophenolat；Diphenyl(phenylsulfanyl)bismuthane
• CAS: 115419-47-1
• 化学式: C₁₈H₁₅BiS
• 分子量: 472.364
• InChiKey: WFFGNIDRXBJBPE-UHFFFAOYSA-M

物化性质

• 熔点：
  83-84 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2-phenylethyl (2-sulfanylidenepyridin-1-yl) carbonate 、 diphenyl(phenylthio)bismuthane 以77%的产率得到
  参考文献：
  名称：

  BARTON, DEREK H. R.;OZBALIK, NUBAR;RAMESH, MANIAN, TETRAHEDRON LETT., 29,(1988) N 8, 857-860

  摘要：

  DOI：
• 作为产物：
  描述：

  三苯基铋 在 ZnCl₂ 作用下， 以 乙醚 、 氯仿 为溶剂， 生成 diphenyl(phenylthio)bismuthane
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Bi: Org.Verb., 1.4.1.2.2.1, page 104 - 109

  摘要：

  DOI：

文献信息

• Insertion of Benzyne into a Bi–S Bond: A New Synthetic Route to <i>ortho</i>-Functionalized Bismuthanes and Its Application to the Synthesis of Dibenzothiophene
  作者：Jing Chen、Toshihiro Murafuji、Ryo Tsunashima

  DOI：10.1021/om200228x

  日期：2011.9.12

  [2-(Ar′S)C6H4]nBiAr3–n have been conveniently synthesized by insertion of benzyne into the bismuth–sulfur bond of (Ar′S)nBiAr3–n (n = 1, 2). A similar insertion takes place when a homologous antimony congener is used, but no reaction is observed with its phosphorus analogue. This suggests a clear difference in the bond strength between pnictogen–sulfur bonds. The carbon–bismuth bond of [2-(2-BrC6H4S)C6H4]nBiAr3–n

  邻芳硫基triarylbismuthanes [2-（AR'S）C 6 H ^ 4 ] Ñ BIAR 3- Ñ已经由苯炔插入被方便地合成到（AR'S）的铋-硫键Ñ BIAR 3- Ñ（Ñ = 1、2）。当使用同源锑同源物时，发生了类似的插入，但是未观察到与其磷类似物的反应。这表明光子-硫键之间的键强度存在明显差异。[2-（2-BrC 6 H 4 S）C 6 H 4 ] n BiAr 3– n的碳-铋键经历钯催化的分子内交叉偶联，以高收率生产二苯并噻吩。对2-（2-BrC 6 H 4 S）C 6 H 4 BiTol 2（Tol = 4-MeC 6 H 4）进行的X射线晶体学研究表明，该分子以二聚体结构存在，其中六个杂原子包括铋，硫和溴通过未键合的分子内铋-硫和分子间的硫-溴和溴-溴相互作用而连接。
• Development of an Arylthiobismuthine Cocatalyst in Organobismuthine-Mediated Living Radical Polymerization: Applications for Synthesis of Ultrahigh Molecular Weight Polystyrenes and Polyacrylates
  作者：Eiichi Kayahara、Shigeru Yamago

  DOI：10.1021/ja8092899

  日期：2009.2.25

  Diphenyl(2,6-dimesitylphenylthio)bismuthine (1a) serves as an excellent cocatalyst in organo-bismuthine-mediated living radical polymerization (BIRP). Both low and high molecular weight polystyrenes and poly(butyl acrylate)s (PBAs) with controlled molecular weights and low polydispersity indexes (PDIs) were synthesized by the addition of a catalytic amount of 1 a to an organobismuthine chain-transfer agent, methyl 2-dimethylbismuthanyl-2-methylpropionate (3). The number-average molecular weight (M,,) of the resulting polymers increases linearly with the monomer/3 ratio. Structurally well-defined polystyrenes with M-n's in the range from 1.0 x 10(4) to 2.0 x 10(5) and PDIs of 1.07-1.15 as well as PBAs with M-n's in the range from 1.2 x 10(4) to 2.8 x 10(6) and PDIs of 1.06-1.43 were successfully prepared under mild thermal conditions. Control experiments suggested that 1 a reversibly reacts with the polymer-end radical to generate an organobismuthine dormant species and 2,6-dimesitylphenylthiyl radical (2a). This reaction avoids the occurrence of chain termination reactions involving the polymer-end radicals and avoids undesired loss of the bismuthanyl polymer end group. The bulky 2,6-dimesitylphenyl group attached to the sulfur atom may prevent the addition of thiyl radicals to the vinyl monomers to generate new polymer chains.
• The Products of the Cleavage of Triarylbismuth Derivatives by —SH-Containing Compounds¹
  作者：Henry Gilman、Harry L. Yale

  DOI：10.1021/ja01150a134

  日期：1951.6
• Calderazzo, Fausto; Morvillo, Antonino; Pelizzi, Giancarlo, Inorganic Chemistry, 1988, vol. 27, # 21, p. 3730 - 3733
  作者：Calderazzo, Fausto、Morvillo, Antonino、Pelizzi, Giancarlo、Poli, Rinaldo、Ungari, Fausto

  DOI：——

  日期：——
• Investigating intermolecular bonding in diphenylbismuth(III) chalcogenolates: X-ray crystal structures of (Ph2BiSR′) (R′=Ph; 2,6-Me2C6H3)
  作者：Glen G. Briand、Andreas Decken、Nicole M. Hunter、Graham M. Lee、Jennifer A. Melanson、Evan M. Owen

  DOI：10.1016/j.poly.2011.11.011

  日期：2012.1

  The reaction of Ph2BiCl with (PhS)Li or (2,6-Me2C6H3S)Li yielded [Ph2BiSPh](infinity), (7) or Ph2BiS(2,6-Me2C6H3)] (8), respectively. Both compounds have been characterized by elemental analysis, melting point, FT-IR, FT-Raman, solution H-1 and C-13H-1) NMR, and X-ray crystallography. The solid-state structure of 7 is polymeric via long intermolecular Bi center dot center dot center dot S interactions and mu-SPh groups, yielding a distorted psi-trigonal bipyramidal C2S2 bonding environment for bismuth. Increasing steric bulk at the phenyl thiolate ligand in 8 results in the isolation of a monomeric species, which exhibits a distorted psi-tetrahedral C2S bonding environment for bismuth. Comparison to previously reported structures of diorganobismuth chalcogenolates shows the effect of altering the chalcogen on intermolecular Bi center dot center dot center dot E (E = O, S, Se) bond formation. OFT calculations are employed to rationalize the bonding environments at bismuth and the observed polymeric structures. This work represents the first examples of structurally characterized R2BiSR' species and advances our understanding of intermolecular bonding in bismuth chalcogenolates. (C) 2011 Elsevier Ltd. All rights reserved.