1,1-bis(tert-butylperoxy)cyclooctane | 146983-17-7

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: 1,1-bis(tert-butylperoxy)cyclooctane
• CAS: 146983-17-7
• 化学式: C₁₆H₃₂O₄
• 分子量: 288.428
• InChiKey: MCLXZGJDXCHKCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  叔丁基过氧化氢 、 环辛酮 在 硫酸 作用下， 以 Petroleum ether 为溶剂， 反应 1.5h， 生成 1,1-bis(tert-butylperoxy)cyclooctane
  参考文献：
  名称：

  Substituent effects on the decomposition of bis(tert-butylperoxy)cycloalkanes

  摘要：

  Decompositions of bis(tert-butylperoxy)cycloalkanes have been carried out in cumene and n-alkanes at temperatures of 80-120-degrees-C and have been compared mainly with the decomposition of tert-alkyl tert-butyl peroxides in order to investigate substituent effects on the homolytic scission of one O-O bond in gem-diperoxides. The decomposition rates of bis(tert-butylperoxy)cycloalkanes are much faster than those of tert-alkyl tert-butyl peroxides; the decomposition rates of the cycloalkanes decrease in the following order: cyclopentane > 3,5,5-trimethylcyclohexane > cyclohexane > cyclooctane > cyclododecane. The effect of ring size on the decomposition and the isokinetic relationships between the activation parameters suggest that stabilization of the transition state by electron donation from the cycloalkyl substituents and repulsion between lone-pair electrons on different peroxy oxygen atoms in the ground state are important factors in the decomposition of gem-diperoxides.

  DOI：

  10.1021/jo00059a029

文献信息

• Synthesis of Geminal Bisperoxides by Acid-Catalyzed Reaction of Acetals and Enol Ethers with <i>tert</i>-Butyl Hydroperoxide
  作者：Alexander Terent’ev、Alexander Kutkin、Nikolay Troizky、Yuri Ogibin、Gennady Nikishin

  DOI：10.1055/s-2005-872093

  日期：——

  A new efficient procedure was developed for the synthesis of geminal bisperoxides by reaction of ketals and enol ethers with tert-butyl hydroperoxide catalyzed by protic or Lewis acids.

  通过缩酮和烯醇醚与叔丁基过氧化氢在质子酸或路易斯酸的催化下反应，开发了一种新的有效合成双过氧化物的方法。
• Substituent effects on the decomposition of bis(tert-butylperoxy)cycloalkanes
  作者：Kazuo Matsuyama、Hiromi Kumura

  DOI：10.1021/jo00059a029

  日期：1993.3

  Decompositions of bis(tert-butylperoxy)cycloalkanes have been carried out in cumene and n-alkanes at temperatures of 80-120-degrees-C and have been compared mainly with the decomposition of tert-alkyl tert-butyl peroxides in order to investigate substituent effects on the homolytic scission of one O-O bond in gem-diperoxides. The decomposition rates of bis(tert-butylperoxy)cycloalkanes are much faster than those of tert-alkyl tert-butyl peroxides; the decomposition rates of the cycloalkanes decrease in the following order: cyclopentane > 3,5,5-trimethylcyclohexane > cyclohexane > cyclooctane > cyclododecane. The effect of ring size on the decomposition and the isokinetic relationships between the activation parameters suggest that stabilization of the transition state by electron donation from the cycloalkyl substituents and repulsion between lone-pair electrons on different peroxy oxygen atoms in the ground state are important factors in the decomposition of gem-diperoxides.