o-(Prop-2-enyloxy)phenyllead Triacetate | 151414-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: o-(Prop-2-enyloxy)phenyllead Triacetate
• 英文别名: Plumbane, tris(acetyloxy)[2-(2-propenyloxy)phenyl]-；[diacetyloxy-(2-prop-2-enoxyphenyl)plumbyl] acetate
• CAS: 151414-77-6
• 化学式: C₁₅H₁₈O₇Pb
• 分子量: 517.504
• InChiKey: UZABPDNCJDSWTD-UHFFFAOYSA-K

物化性质

• 沸点：
  448.7±47.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  o-(Prop-2-enyloxy)phenyllead Triacetate 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 2.5h， 以74%的产率得到o-(prop-2-enyloxy)phenyl azide
  参考文献：
  名称：

  Mechanism of arylation of nucleophiles by aryllead triacetates. Part 1. Exclusion of a pathway involving aryl free radicals

  摘要：

  o-(Prop-2-enyloxy)phenyllead triacetate 6. which was obtained by treatment of the corresponding boronic acid with lead tetraacetate, has been shown to react with iodide and azide ions, 2,4,6-trimethylphenol, ethyl 2-oxocyclopentanecarboxylate, and the sodium salt of 2-nitropropane to give only those products which, in a formal sense, are derived by direct nucleophilic displacement of the Pb(OAc), group. The complete absence of 3-substituted dihydrobenzofurans among the products is strong evidence that aryl free radicals are not involved in the arylation reactions of aryllead triacetates.

  DOI：

  10.1039/p19930001673
• 作为产物：
  描述：

  mercury(II) diacetate 、 lead(IV) tetraacetate 、 2-烯丙氧基苯硼酸 以 氯仿 为溶剂， 以81%的产率得到o-(Prop-2-enyloxy)phenyllead Triacetate
  参考文献：
  名称：

  Mechanism of arylation of nucleophiles by aryllead triacetates. Part 1. Exclusion of a pathway involving aryl free radicals

  摘要：

  o-(Prop-2-enyloxy)phenyllead triacetate 6. which was obtained by treatment of the corresponding boronic acid with lead tetraacetate, has been shown to react with iodide and azide ions, 2,4,6-trimethylphenol, ethyl 2-oxocyclopentanecarboxylate, and the sodium salt of 2-nitropropane to give only those products which, in a formal sense, are derived by direct nucleophilic displacement of the Pb(OAc), group. The complete absence of 3-substituted dihydrobenzofurans among the products is strong evidence that aryl free radicals are not involved in the arylation reactions of aryllead triacetates.

  DOI：

  10.1039/p19930001673

文献信息

• Mechanism of arylation of nucleophiles by aryllead triacetates. Part 2. Support for a ligand coupling process and X-ray molecular structure of (p-methoxyphenyl)-α-methylphenacyllead (<scp>IV</scp>) diacetate
  作者：Jacqueline Morgan、Irmi Buys、Trevor W. Hambley、John T. Pinhey

  DOI：10.1039/p19930001677

  日期：——

  In the presence of boron trifluoride–diethyl ether complex p-methoxyphenyllead triacetate 4 and the propiophenone silyl enol ether 6 were found to undergo a rapid reaction to give (p-methoxyphenyl)-α-methylphenacyllead diacetate 9 in high yield. Analogous products, 5, 10 and 11 respectively, were formed when the silyl enol ethers of acetophenone, butyrophenone and isobutyrophenone were treated under

  发现在三氟化硼-乙醚复合物存在下，对甲氧基苯基三乙酸铅4和丙苯甲硅烷基烯醇醚6发生快速反应，从而以高收率得到（对甲氧基苯基）-α-甲基苯甲酰基乙酸铅9。类似产品，5，10和11分别表示当苯乙酮，丁酮和异丁酰苯的甲硅烷基烯醇醚，用芳基铅化合物相同的条件下处理形成4。所述diorganolead二乙酸酯9，10和11相对不稳定，在氯仿中于60°C加热时会生成许多产品。在每种情况下，均会显着消除Pb（OAc）2，并形成配体偶联产物脱氧安息香。为探测偶联反应机理而生产的α-甲基苯甲酰基（邻-丙-2-烯氧基）苯基二乙酸铅21的行为与化合物9相似，没有提供二氢苯并呋喃衍生物。因此，似乎在这些热反应中最有可能没有产生芳基自由基，并且提出了配体偶联机理。