1,2-戴奧辛

1,2-戴奧辛(英語:1,2-Dioxin)是一種雜環有機反芳香性[1]化合物化學式為C4H4O2。它是1,4-戴奧辛同分異構物

1,2-戴奧辛
IUPAC名
1,2-Dioxine
1,2-二氧雜環己熳
系統名
1,2-Dioxacyclohexa-3,5-diene
1,2-二氧雜環-3,5-己二烯
識別
CAS編號 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
性質
化學式 C4H4O2
莫耳質量 84.07 g·mol−1
相關物質
相關化學品 二苯駢對戴奧辛
1,4-戴奧辛
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

由於它類似於過氧化物的性質,1,2-戴奧辛非常不穩定,仍未分離。根據計算,它會快速異構化成2-丁烯二醛。[2]取代基衍生物也非常不穩定,例如1,4-二苯基-2,3-苯駢戴奧辛。[3]1990年,3,6-二(對甲苯基)-1,2-戴奧辛被誤認為是第一個穩定的衍生物,[4]之後表明初始化合物不是1,2-戴奧辛的衍生物,而是一個熱力學上更穩定的二酮[5]

參考文獻

  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. (原始內容存檔於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.