1,2-二𫫇英(英语:1,2-Dioxin)是一种杂环有机反芳香性[1]化合物化学式为C4H4O2。它是1,4-二𫫇英同分异构体

1,2-二𫫇英
IUPAC名
1,2-Dioxine
1,2-二氧杂环己熳
系统名
1,2-Dioxacyclohexa-3,5-diene
1,2-二氧杂环-3,5-己二烯
识别
CAS号 289-87-2  checkY
PubChem 15559065
ChemSpider 10606250
SMILES
 
  • O1OC=CC=C1
InChI
 
  • 1/C4H4O2/c1-2-4-6-5-3-1/h1-4H
InChIKey VCZQYTJRWNRPHF-UHFFFAOYAH
性质
化学式 C4H4O2
摩尔质量 84.07 g·mol−1
相关物质
相关化学品 二苯并对二𫫇英
1,4-二𫫇英
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

由于它类似于过氧化物的性质,1,2-二𫫇英非常不稳定,仍未分离。根据计算,它会快速异构化成2-丁烯二醛。[2]取代基衍生物也非常不稳定,例如1,4-二苯基-2,3-苯并二𫫇英。[3]1990年,3,6-二(对甲苯基)-1,2-二𫫇英被误认为是第一个稳定的衍生物,[4]之后表明初始化合物不是1,2-二𫫇英的衍生物,而是一个热力学上更稳定的二酮[5]

参考文献

编辑
  1. ^ Pelloni, Stefano; Faglioni, Francesco; Lazzeretti, Paolo. Parity violation energies of C4H4X2 molecules for X = O, S, Se, Te and Po. Molecular Physics. 2013-09-01, 111 (16-17): 2387–2391. ISSN 0026-8976. doi:10.1080/00268976.2013.794396. 
  2. ^ Matsumoto, M. Product Class 1: 1,2-Dioxins and Benzo- and Dibenzo- Fused Derivatives. Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 16: Six-Membered Hetarenes with Two Identical Heteroatoms. Georg Thieme Verlag. 2014: 13 [2020-06-12]. ISBN 9783131718815. (原始内容存档于2022-03-27). 
  3. ^ Smith, Jimmie P.; Schrock, Alan K.; Schuster, Gary B. Chemiluminescence of organic peroxides. Thermal generation of an o-xylylene peroxide. Journal of the American Chemical Society. 1982, 104 (4): 1041. doi:10.1021/ja00368a021. .
  4. ^ Shine, Henry J.; Zhao, Da Chuan. Electron transfer to excited doublet states. Photoirradiation of 10-methylphenothiazine cation radical perchlorate in solutions of phenylacetylene and p-tolylacetylene in acetonitrile. The Journal of Organic Chemistry. 1990, 55 (13): 4086. doi:10.1021/jo00300a026. .
  5. ^ Block, Eric; Shan, Zhixing; Glass, Richard S.; Fabian, Jürgen. Revised Structure of a Purported 1,2-Dioxin: A Combined Experimental and Theoretical Study. The Journal of Organic Chemistry. 2003, 68 (10): 4108–11. PMID 12737603. doi:10.1021/jo034305i.