diphenyl(2,6-dimesitylphenylthio)bismuthine | 1056475-42-3

• 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: diphenyl(2,6-dimesitylphenylthio)bismuthine
• 英文别名: (2,6-dimesitylphenylthio)diphenylbismuthane；[2,6-Bis(2,4,6-trimethylphenyl)phenyl]sulfanyl-diphenylbismuthane；[2,6-bis(2,4,6-trimethylphenyl)phenyl]sulfanyl-diphenylbismuthane
• CAS: 1056475-42-3
• 化学式: C₃₆H₃₅BiS
• 分子量: 708.72
• InChiKey: UVLZWPXVYHYUGM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  8.77
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 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-cyano-1-methyl-ethyl 、 diphenyl(2,6-dimesitylphenylthio)bismuthine 在 偶氮二异丁腈 作用下， 生成 2-diphenylbismuthanyl-2-methylpropionitrile
  参考文献：
  名称：

  Development of an Arylthiobismuthine Cocatalyst in Organobismuthine-Mediated Living Radical Polymerization: Applications for Synthesis of Ultrahigh Molecular Weight Polystyrenes and Polyacrylates

  摘要：

  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.

  DOI：

  10.1021/ja8092899
• 作为产物：
  描述：

  diphenylbismuthanyl bromide 、 2,6-bis(2,4,6-trimethylphenyl)phenylthiol 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 以69%的产率得到diphenyl(2,6-dimesitylphenylthio)bismuthine
  参考文献：
  名称：

  Development of an Arylthiobismuthine Cocatalyst in Organobismuthine-Mediated Living Radical Polymerization: Applications for Synthesis of Ultrahigh Molecular Weight Polystyrenes and Polyacrylates

  摘要：

  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.

  DOI：

  10.1021/ja8092899

文献信息

• LIVING RADICAL POLYMERIZATION PROMOTER
  申请人：Otsuka Chemical Co., Ltd.

  公开号：EP2133357B1

  公开（公告）日：2016-11-16
• 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.