cis-3,5-bis(4-chlorophenyl)-1,2-dioxolane | 143447-47-6

• 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: cis-3,5-bis(4-chlorophenyl)-1,2-dioxolane
• 英文别名: (3S,5R)-3,5-bis(4-chlorophenyl)dioxolane
• CAS: 143447-47-6
• 化学式: C₁₅H₁₂Cl₂O₂
• 分子量: 295.165
• InChiKey: XTWCRDLPDGNFMJ-GASCZTMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  rac-trans-1,2-bis(4-chlorophenyl)cyclopropane 在 magnesium(II) perchlorate 、 9,10-二氰基蒽 、 氧气 作用下， 以 乙腈 为溶剂， 反应 1.33h， 生成 4-氯苯甲醛 、 对氯苯乙酮 、 cis-3,5-bis(4-chlorophenyl)-1,2-dioxolane 、 trans-3,5-bis(4-chlorophenyl)-1,2-dioxolane
  参考文献：
  名称：

  Salt effect on the 9,10-dicyanoanthracene-sensitized photooxygenation of 1,2-diarylcyclopropanes and the photodecomposition of 3,5-diaryl-1,2-dioxolanes

  摘要：

  The 9,10-dicyanoanthracene (DCA)-sensitized photooxygenation of less electron-rich 1,2-diarylcyclopropanes 1 such as 1,2-diphenylcyclopropanes and 1,2-bis(4-chlorophenyl)cyclopropanes in the presence of Mg(ClO4)2 gave cis- and trans-3,5-diaryl-1,2-dioxolanes as major products. However, in the absence of Mg(ClO4)2, the Photooxygenation did not afford 1,2-dioxolanes, but their decomposition products, 1,3-diaryl-1-hydroxypropan-3-ones 5, aryl aldehydes 6, and aryl methyl ketones 7. The DCA-sensitized photodecomposition of 1,2-dioxolanes also gave 5-7. This photoreaction was suppressed by the addition Of Mg(ClO4)2. The DCA-sensitized photooxygenation of 1 proceeds via radical cations that are generated by photoinduced electron-transfer from 1 to the excited singlet 1DCA*. The DCA-sensitized photodecomposition of 1,2-dioxolanes occurs via exciplexes that are formed between 1,2-dioxolanes and 1DCA* or energy-transfer from the excited triplet 3DCA* to 1,2-dioxolanes.

  DOI：

  10.1021/jo00046a014

文献信息

• Salt effect on the 9,10-dicyanoanthracene-sensitized photooxygenation of 1,2-diarylcyclopropanes and the photodecomposition of 3,5-diaryl-1,2-dioxolanes
  作者：Toshiyuki Tamai、Kazuhiko Mizuno、Isao Hashida、Yoshio Otsuji

  DOI：10.1021/jo00046a014

  日期：1992.9

  The 9,10-dicyanoanthracene (DCA)-sensitized photooxygenation of less electron-rich 1,2-diarylcyclopropanes 1 such as 1,2-diphenylcyclopropanes and 1,2-bis(4-chlorophenyl)cyclopropanes in the presence of Mg(ClO4)2 gave cis- and trans-3,5-diaryl-1,2-dioxolanes as major products. However, in the absence of Mg(ClO4)2, the Photooxygenation did not afford 1,2-dioxolanes, but their decomposition products, 1,3-diaryl-1-hydroxypropan-3-ones 5, aryl aldehydes 6, and aryl methyl ketones 7. The DCA-sensitized photodecomposition of 1,2-dioxolanes also gave 5-7. This photoreaction was suppressed by the addition Of Mg(ClO4)2. The DCA-sensitized photooxygenation of 1 proceeds via radical cations that are generated by photoinduced electron-transfer from 1 to the excited singlet 1DCA*. The DCA-sensitized photodecomposition of 1,2-dioxolanes occurs via exciplexes that are formed between 1,2-dioxolanes and 1DCA* or energy-transfer from the excited triplet 3DCA* to 1,2-dioxolanes.