1,3-propanediylbis{triphenylplumbane} | 134879-53-1

• 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: 1,3-propanediylbis{triphenylplumbane}
• 英文别名: hexa-Pb-phenyl-Pb,Pb'-propanediyl-bis plumbane；Hexa-Pb-phenyl-Pb,Pb'-propandiyl-bis-plumban；1,3-Bis-triphenylplumbyl-propan；1,3-Bis(triphenylplumbyl)propane；triphenyl(3-triphenylplumbylpropyl)plumbane
• CAS: 134879-53-1
• 化学式: C₃₉H₃₆Pb₂
• 分子量: 919.115
• InChiKey: JGKCHZKFOVKAKC-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95 °C
• 沸点：
  724.2±70.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3-propanediylbis{triphenylplumbane} 在 I₂ 作用下， 以 氘代氯仿 为溶剂， 生成 (C₆H₅)2IPbCH₂CH₂CH₂PbI(C₆H₅)2
  参考文献：
  名称：

  尝试合成1,3,5-三苯基-2,4,9-trithia-1,3,5-triplumbaadamantane。有机碘化物分解

  摘要：

  MNDO calculations suggest that the strength of the bridgehead carbon-hydrogen bond in 2,4,9-trithia-1,3,5-triplumbaadamantane (2a) should be only 54 kcal/mol and the hydride affinity of the corresponding bridgehead cation 2a+ should be only 215 kcal/mol. As a donor of hydrogen atoms or hydride, plumbaadamantane 2a should therefore be even more reactive than the analogous stannaadamantane 1a. Unfortunately, substituted derivative 2b could not be prepared from (Ph3PbCH2)3CH by controlled iodinolysis followed by treatment of the intermediate hexaiodide (PhI2PbCH2)3CH with Ph3SnSSnPh3. This failure results in part from the tendency of organolead diiodides R2PbI2 to undergo redistribution reactions that produce unstable triiodides RPbI3. Diiodides capable of intramolecular redistributions are particularly reactive. The resulting triiodides then decompose by a formal reductive elimination of RI and PbI2. Since the iodinolysis of (cyclopropylmethyl)triphenylplumbane (11) yields mainly (iodomethyl)cyclopropane instead of ring-opened products derived from cyclopropylmethyl cations or radicals, we suggest that the reductive elimination of RI and PbI2 from RPbI3 is concerted.

  DOI：

  10.1021/om00054a069
• 作为产物：
  描述：

  1,3-二溴丙烷 、 alkaline earth salt of/the/ methylsulfuric acid 生成 1,3-propanediylbis{triphenylplumbane}
  参考文献：
  名称：

  The Preparation of Organolead Compounds Containing Water-solubilizing Groups

  摘要：

  DOI：

  10.1021/ja01143a030

文献信息

• The Preparation of Organolead Compounds Containing Water-solubilizing Groups
  作者：Henry Gilman、Lawrence Summers

  DOI：10.1021/ja01143a030

  日期：1952.12
• Attempted synthesis of 1,3,5-triphenyl-2,4,9-trithia-1,3,5-triplumbaadamantane. Decomposition of organolead iodides
  作者：Michio Kobayashi、Stephan Latour、James D. Wuest

  DOI：10.1021/om00054a069

  日期：1991.8

  MNDO calculations suggest that the strength of the bridgehead carbon-hydrogen bond in 2,4,9-trithia-1,3,5-triplumbaadamantane (2a) should be only 54 kcal/mol and the hydride affinity of the corresponding bridgehead cation 2a+ should be only 215 kcal/mol. As a donor of hydrogen atoms or hydride, plumbaadamantane 2a should therefore be even more reactive than the analogous stannaadamantane 1a. Unfortunately, substituted derivative 2b could not be prepared from (Ph3PbCH2)3CH by controlled iodinolysis followed by treatment of the intermediate hexaiodide (PhI2PbCH2)3CH with Ph3SnSSnPh3. This failure results in part from the tendency of organolead diiodides R2PbI2 to undergo redistribution reactions that produce unstable triiodides RPbI3. Diiodides capable of intramolecular redistributions are particularly reactive. The resulting triiodides then decompose by a formal reductive elimination of RI and PbI2. Since the iodinolysis of (cyclopropylmethyl)triphenylplumbane (11) yields mainly (iodomethyl)cyclopropane instead of ring-opened products derived from cyclopropylmethyl cations or radicals, we suggest that the reductive elimination of RI and PbI2 from RPbI3 is concerted.