Trimethylethylene ozonide | 2425-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三氧戊环
• 英文名称: Trimethylethylene ozonide
• 英文别名: 2-Methyl-but-2-en-ozonid；trimethyl-[1,2,4]trioxolane；3,3,5-Trimethyl-1,2,4-trioxolane
• CAS: 2425-42-5
• 化学式: C₅H₁₀O₃
• 分子量: 118.133
• InChiKey: UWERKMHVBPTSHC-UHFFFAOYSA-N

物化性质

• 沸点：
  91.6±29.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-二甲基-2-丁烯 、 乙醛 以 正己烷 为溶剂， 反应 0.05h， 生成 2,3-二甲基-2,3-环氧丁烷 、 丙酮过氧化物 、 Trimethylethylene ozonide
  参考文献：
  名称：

  The ozonolysis of tetramethylethylene. Concentration and temperature effects

  摘要：

  The products of the ozonolysis of tetramethylethylene in hexane or methylene chloride are remarkably dependent on the concentration of tetramethylethylene. Ozonolysis in neat tetramethylethylene gives mostly tetramethylethylene epoxide as product. As the concentration of tetramethylethylene is reduced, more acetone diperoxide is formed until it becomes the major product. The reaction also produces 3-hydroperoxy-2,3-dimethyl-1-butene. The product distribution is also quite dependent on reaction temperature. At a given concentration of the alkene the epoxide yield decreases as the temperature is lowered. Simultaneously the acetone diperoxide yield increases with lower temperature. The results are explained by postulating that energy-rich acetone oxide can be partially converted to dimethyldioxirane which is primarily responsible for the epoxidation. The proposed reaction scheme also has acetone oxide dimerize in a stepwise manner to give an intermediate which can either close to give diperoxide or lose singlet oxygen. The singlet oxygen would then react with tetramethylethylene to give the hydroperoxide.

  DOI：

  10.1021/jo00054a010

文献信息

• The ozonolysis of tetramethylethylene. Concentration and temperature effects
  作者：Robert W. Murray、Wei Kong、Shirish N. Rajadhyaksha

  DOI：10.1021/jo00054a010

  日期：1993.1

  The products of the ozonolysis of tetramethylethylene in hexane or methylene chloride are remarkably dependent on the concentration of tetramethylethylene. Ozonolysis in neat tetramethylethylene gives mostly tetramethylethylene epoxide as product. As the concentration of tetramethylethylene is reduced, more acetone diperoxide is formed until it becomes the major product. The reaction also produces 3-hydroperoxy-2,3-dimethyl-1-butene. The product distribution is also quite dependent on reaction temperature. At a given concentration of the alkene the epoxide yield decreases as the temperature is lowered. Simultaneously the acetone diperoxide yield increases with lower temperature. The results are explained by postulating that energy-rich acetone oxide can be partially converted to dimethyldioxirane which is primarily responsible for the epoxidation. The proposed reaction scheme also has acetone oxide dimerize in a stepwise manner to give an intermediate which can either close to give diperoxide or lose singlet oxygen. The singlet oxygen would then react with tetramethylethylene to give the hydroperoxide.