1,2-Dioxolan | 4362-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 1,2-Dioxolan
• 英文别名: (+)-cis-dioxolane；1,2-Dioxolane；dioxolane
• CAS: 4362-13-4
• 化学式: C₃H₆O₂
• 分子量: 74.0794
• InChiKey: SNQXJPARXFUULZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  5
• 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：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-iodopropyl tert-butyl peroxide 在 silver trifluoroacetate 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 1,2-Dioxolan
  参考文献：
  名称：

  Oxymetalation. 20. Conversion of cyclopropanes into 1,2-dioxolanes via tert-butyl peroxymercuration, bromodemercuration, and silver salt induced cyclization

  摘要：

  DOI：

  10.1021/jo00361a034
• 作为试剂：
  描述：

  bis(4-tert-butylphenyl)iodonium chloride 在 1,2-Dioxolan 、 偶氮二异丁腈 作用下， 反应 7.0h， 生成 3-氯丙酸 、 叔丁基苯 、 1-叔丁基-3-碘苯 、 4-叔丁基氯化苯
  参考文献：
  名称：

  Initiation of cationic polymerization of cyclic ethers by redox radical-chain reactions of onium salts

  摘要：

  Redox radical-chain reactions of diaryliodonium halides (Ar2I+X-) with tetrahydrofuran (THF) and 1,3-dioxolane to give arenes (ArH) and iodoarenes (ArI) are reported. When the reactions are initiated by irradiation at 313 nm, the quantum yield for the formation of iodoarene is substantially greater than 1 (PHI almost-equal-to 2-20). Nonphotochemical radical initiators give the same reaction, showing that the photochemical step is simply an initiation step. The key propagation step in these reactions is a single-electron reduction of the onium salts by ether-derived radicals. The photoinitiated reaction with THF follows zero-order kinetics, showing that termination does not compete with electron transfer. In addition, the same nonphotochemical conditions that give radical-chain reduction of the diaryliodonium halides give rapid cationic polymerization of the ethers when the iodonium hexafluorophosphates are used. These observations establish the connection between the redox chemistry of the iodonium salt and the cationic polymerization of the ethers. The polymerization of THF by iodonium salt in the presence of free radicals is accelerated by the addition of trimethyl phosphite (TMP). Furthermore, triarylsulfonium salts will initiate polymerization of THF in the presence of TMP and radical sources. Therefore, redox-chain reduction of these onium salts by TMP can also initiate cationic polymerization of the cyclic ethers.

  DOI：

  10.1021/jo00085a030

文献信息

• BLOODWORTH, A. J.;CHAN, KAM, HUNG;COOKSEY, CH. J., J. ORG. CHEM., 1986, 51, N 11, 2110-2115
  作者：BLOODWORTH, A. J.、CHAN, KAM, HUNG、COOKSEY, CH. J.

  DOI：——

  日期：——
• Oxymetalation. 20. Conversion of cyclopropanes into 1,2-dioxolanes via tert-butyl peroxymercuration, bromodemercuration, and silver salt induced cyclization
  作者：A. J. Bloodworth、Kam Hung Chan、Christopher J. Cooksey

  DOI：10.1021/jo00361a034

  日期：1986.5