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{{For|other dioxin compounds|dioxin}} {{For|other dioxin compounds|dioxin}}


'''1,2-Dioxin''' is a ], ], ]<ref>{{Cite journal |last=Pelloni |first=Stefano |last2=Faglioni |first2=Francesco |last3=Lazzeretti |first3=Paolo |date=2013-09-01 |title=Parity violation energies of C4H4X2 molecules for X = O, S, Se, Te and Po |url=https://doi.org/10.1080/00268976.2013.794396 |journal=Molecular Physics |volume=111 |issue=16-17 |pages=2387–2391 |doi=10.1080/00268976.2013.794396 |issn=0026-8976}}</ref> ] with the ] C{{sub|4}}H{{sub|4}}O{{sub|2}}. It is an ]ic form of ] (or ''p''-dioxin). '''1,2-Dioxin''' is a ], ], ]<ref>{{Cite journal |last1=Pelloni |first1=Stefano |last2=Faglioni |first2=Francesco |last3=Lazzeretti |first3=Paolo |date=2013-09-01 |title=Parity violation energies of C4H4X2 molecules for X = O, S, Se, Te and Po |url=https://doi.org/10.1080/00268976.2013.794396 |journal=Molecular Physics |volume=111 |issue=16–17 |pages=2387–2391 |doi=10.1080/00268976.2013.794396 |s2cid=100861633 |issn=0026-8976}}</ref> ] with the ] C{{sub|4}}H{{sub|4}}O{{sub|2}}. It is an ]ic form of ] (or ''p''-dioxin).


Due to its ]-like characteristics, 1,2-dioxin is very unstable and has not been isolated. Calculations suggest that it would isomerize rapidly into but-2-enedial.<ref>{{Cite book|last=Matsumoto|first=M.|chapter-url=https://books.google.com/books?id=Ah6GAwAAQBAJ&pg=PA13|title=Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 16: Six-Membered Hetarenes with Two Identical Heteroatoms|publisher=Georg Thieme Verlag|year=2014|isbn=9783131718815|pages=13|chapter=Product Class 1: 1,2-Dioxins and Benzo- and Dibenzo- Fused Derivatives|access-date=2020-06-12}}</ref> Even ] ] are very labile, e.g. 1,4-diphenyl-2,3-benzodioxin.<ref>{{Cite journal | doi = 10.1021/ja00368a021| title = Chemiluminescence of organic peroxides. Thermal generation of an o-xylylene peroxide| journal = Journal of the American Chemical Society| volume = 104| issue = 4| pages = 1041| year = 1982| last1 = Smith| first1 = Jimmie P.| last2 = Schrock| first2 = Alan K.| last3 = Schuster| first3 = Gary B.}}.</ref> Indeed, in 1990, 3,6-bis(''p''-tolyl)-1,2-dioxin was wrongly accounted as the first stable derivative.<ref>{{Cite journal | doi = 10.1021/jo00300a026| title = Electron transfer to excited doublet states. Photoirradiation of 10-methylphenothiazine cation radical perchlorate in solutions of phenylacetylene and p-tolylacetylene in acetonitrile| journal = The Journal of Organic Chemistry| volume = 55| issue = 13| pages = 4086| year = 1990| last1 = Shine| first1 = Henry J.| last2 = Zhao| first2 = Da Chuan}}.</ref> It was subsequently shown that the initial compound was not a derivative of 1,2-dioxin, but a thermodynamically more stable ].<ref>{{Cite journal | doi = 10.1021/jo034305i| pmid = 12737603| title = Revised Structure of a Purported 1,2-Dioxin: A Combined Experimental and Theoretical Study| journal = The Journal of Organic Chemistry| volume = 68| issue = 10| pages = 4108–11| year = 2003| last1 = Block| first1 = Eric| last2 = Shan| first2 = Zhixing| last3 = Glass| first3 = Richard S.| last4 = Fabian| first4 = Jürgen}}</ref> Due to its ]-like characteristics, 1,2-dioxin is very unstable and has not been isolated. Calculations suggest that it would isomerize rapidly into but-2-enedial.<ref>{{Cite book|last=Matsumoto|first=M.|chapter-url=https://books.google.com/books?id=Ah6GAwAAQBAJ&pg=PA13|title=Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 16: Six-Membered Hetarenes with Two Identical Heteroatoms|publisher=Georg Thieme Verlag|year=2014|isbn=9783131718815|pages=13|chapter=Product Class 1: 1,2-Dioxins and Benzo- and Dibenzo- Fused Derivatives|access-date=2020-06-12}}</ref> Even ] ] are very labile, e.g. 1,4-diphenyl-2,3-benzodioxin.<ref>{{Cite journal | doi = 10.1021/ja00368a021| title = Chemiluminescence of organic peroxides. Thermal generation of an o-xylylene peroxide| journal = Journal of the American Chemical Society| volume = 104| issue = 4| pages = 1041| year = 1982| last1 = Smith| first1 = Jimmie P.| last2 = Schrock| first2 = Alan K.| last3 = Schuster| first3 = Gary B.}}.</ref> Indeed, in 1990, 3,6-bis(''p''-tolyl)-1,2-dioxin was wrongly accounted as the first stable derivative.<ref>{{Cite journal | doi = 10.1021/jo00300a026| title = Electron transfer to excited doublet states. Photoirradiation of 10-methylphenothiazine cation radical perchlorate in solutions of phenylacetylene and p-tolylacetylene in acetonitrile| journal = The Journal of Organic Chemistry| volume = 55| issue = 13| pages = 4086| year = 1990| last1 = Shine| first1 = Henry J.| last2 = Zhao| first2 = Da Chuan}}.</ref> It was subsequently shown that the initial compound was not a derivative of 1,2-dioxin, but a thermodynamically more stable ].<ref>{{Cite journal | doi = 10.1021/jo034305i| pmid = 12737603| title = Revised Structure of a Purported 1,2-Dioxin: A Combined Experimental and Theoretical Study| journal = The Journal of Organic Chemistry| volume = 68| issue = 10| pages = 4108–11| year = 2003| last1 = Block| first1 = Eric| last2 = Shan| first2 = Zhixing| last3 = Glass| first3 = Richard S.| last4 = Fabian| first4 = Jürgen}}</ref>

Latest revision as of 23:00, 23 September 2023

1,2-Dioxin
Skeletal formula of 1,2-dioxin
Names
Preferred IUPAC name 1,2-Dioxine
Systematic IUPAC name 1,2-Dioxacyclohexa-3,5-diene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H4O2/c1-2-4-6-5-3-1/h1-4HKey: VCZQYTJRWNRPHF-UHFFFAOYSA-N
  • InChI=1/C4H4O2/c1-2-4-6-5-3-1/h1-4HKey: VCZQYTJRWNRPHF-UHFFFAOYAH
SMILES
  • O1OC=CC=C1
Properties
Chemical formula C4H4O2
Molar mass 84.074 g·mol
Related compounds
Related compounds Dibenzodioxin

1,4-Dioxin

Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound For other dioxin compounds, see dioxin.

1,2-Dioxin is a heterocyclic, organic, antiaromatic compound with the chemical formula C4H4O2. It is an isomeric form of 1,4-dioxin (or p-dioxin).

Due to its peroxide-like characteristics, 1,2-dioxin is very unstable and has not been isolated. Calculations suggest that it would isomerize rapidly into but-2-enedial. Even substituted derivatives are very labile, e.g. 1,4-diphenyl-2,3-benzodioxin. Indeed, in 1990, 3,6-bis(p-tolyl)-1,2-dioxin was wrongly accounted as the first stable derivative. It was subsequently shown that the initial compound was not a derivative of 1,2-dioxin, but a thermodynamically more stable dione.

  • The isomers 1,2-dioxin (left) and 1,4-dioxin (right) The isomers 1,2-dioxin (left) and 1,4-dioxin (right)
  • Structure of the transient 1,4-diphenyl- 2,3-benzodioxin Structure of the transient 1,4-diphenyl- 2,3-benzodioxin
  • Dioxin (1) and dione form (2) Dioxin (1) and dione form (2)

References

  1. Pelloni, Stefano; Faglioni, Francesco; Lazzeretti, Paolo (2013-09-01). "Parity violation energies of C4H4X2 molecules for X = O, S, Se, Te and Po". Molecular Physics. 111 (16–17): 2387–2391. doi:10.1080/00268976.2013.794396. ISSN 0026-8976. S2CID 100861633.
  2. Matsumoto, M. (2014). "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. p. 13. ISBN 9783131718815. Retrieved 2020-06-12.
  3. Smith, Jimmie P.; Schrock, Alan K.; Schuster, Gary B. (1982). "Chemiluminescence of organic peroxides. Thermal generation of an o-xylylene peroxide". Journal of the American Chemical Society. 104 (4): 1041. doi:10.1021/ja00368a021..
  4. Shine, Henry J.; Zhao, Da Chuan (1990). "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. 55 (13): 4086. doi:10.1021/jo00300a026..
  5. Block, Eric; Shan, Zhixing; Glass, Richard S.; Fabian, Jürgen (2003). "Revised Structure of a Purported 1,2-Dioxin: A Combined Experimental and Theoretical Study". The Journal of Organic Chemistry. 68 (10): 4108–11. doi:10.1021/jo034305i. PMID 12737603.


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