1,2-Dioxin

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1,2-Dioxin
Skeletal formula of 1,2-dioxin 1,2-dioxin.svg
Skeletal formula of 1,2-dioxin
1,2-Dioxin-3D-balls 2.png
1,2-Dioxin-3D-spacefill.png
Names
Preferred IUPAC name
1,2-Dioxine
Systematic IUPAC name
1,2-Dioxacyclohexa-3,5-diene
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C4H4O2/c1-2-4-6-5-3-1/h1-4H Yes check.svgY
    Key: VCZQYTJRWNRPHF-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H4O2/c1-2-4-6-5-3-1/h1-4H
    Key: VCZQYTJRWNRPHF-UHFFFAOYAH
  • O1OC=CC=C1
Properties
C4H4O2
Molar mass 84.074 g·mol−1
Related compounds
Related compounds
Dibenzodioxin

1,4-Dioxin

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,2-Dioxin is a heterocyclic, organic, antiaromatic [1] compound with the chemical formula C4H4O2. It is an isomeric form of 1,4-dioxin (or p-dioxin).

1,2-Dioxin (left) and 1,4-dioxin (right) Dioxin isomers.svg
1,2-Dioxin (left) and 1,4-dioxin (right)

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. [2] Even substituted derivatives, such as 1,4-diphenyl-2,3-benzodioxin, are very labile. [3]

Structure of the transient 1,4-diphenyl-2,3-benzodioxin 1,4-diphenyl-2,3-benzodioxin.svg
Structure of the transient 1,4-diphenyl-2,3-benzodioxin

In 1990, 3,6-bis(p-tolyl)-1,2-dioxin (1) was incorrectly reported as the first stable derivative. [4] It was subsequently shown that the initial compound was not a derivative of 1,2-dioxin, but a thermodynamically more stable dione (2). [5]

Dioxin (1) and dione form (2) Revised structure 1,2-Dioxin.svg
Dioxin (1) and dione form (2)

Related Research Articles

The quinones are a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds", resulting in "a fully conjugated cyclic dione structure". The archetypical member of the class is 1,4-benzoquinone or cyclohexadienedione, often called simply "quinone". Other important examples are 1,2-benzoquinone (ortho-quinone), 1,4-naphthoquinone and 9,10-anthraquinone.

<span class="mw-page-title-main">Epoxide</span> Organic compounds with a carbon-carbon-oxygen ring

In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile.

Cubane is a synthetic hydrocarbon compound with the formula C8H8. It consists of eight carbon atoms arranged at the corners of a cube, with one hydrogen atom attached to each carbon atom. A solid crystalline substance, cubane is one of the Platonic hydrocarbons and a member of the prismanes. It was first synthesized in 1964 by Philip Eaton and Thomas Cole. Before this work, Eaton believed that cubane would be impossible to synthesize due to the "required 90 degree bond angles". The cubic shape requires the carbon atoms to adopt an unusually sharp 90° bonding angle, which would be highly strained as compared to the 109.45° angle of a tetrahedral carbon. Once formed, cubane is quite kinetically stable, due to a lack of readily available decomposition paths. It is the simplest hydrocarbon with octahedral symmetry.

<span class="mw-page-title-main">Dicarbonyl</span> Molecule containing two adjacent C=O groups

In organic chemistry, a dicarbonyl is a molecule containing two carbonyl groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls are in close enough proximity that their reactivity is changed, such as 1,2-, 1,3-, and 1,4-dicarbonyls. Their properties often differ from those of monocarbonyls, and so they are usually considered functional groups of their own. These compounds can have symmetrical or unsymmetrical substituents on each carbonyl, and may also be functionally symmetrical or unsymmetrical.

<span class="mw-page-title-main">Silabenzene</span> Chemical compound

A silabenzene is a heteroaromatic compound containing one or more silicon atoms instead of carbon atoms in benzene. A single substitution gives silabenzene proper; additional substitutions give a disilabenzene, trisilabenzene, etc.

<span class="mw-page-title-main">Dibenzo-1,4-dioxin</span> Chemical compound

Dibenzo-1,4-dioxin, also dibenzodioxin or dibenzo-p-dioxin (dibenzo-para-dioxin), is a polycyclic heterocyclic organic compound in which two benzene rings are connected by a 1,4-dioxin ring. Its molecular formula is C12H8O2. The two oxygen atoms occupy opposite (para-) positions in the six-membered dioxin ring.

<span class="mw-page-title-main">1,4-Benzoquinone</span> Chemical compound

1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound.

1,2-Benzoquinone, also called ortho-benzoquinone, is an organic compound with formula C6H4O2. It is one of the two isomers of quinone, the other being 1,4-benzoquinone. It is a red volatile solid that is soluble in water and diethyl ether. It is rarely encountered because of its instability, but it is of fundamental interest as the parent compound of many derivatives which are known.

<span class="mw-page-title-main">Dakin oxidation</span> Organic redox reaction that converts hydroxyphenyl aldehydes or ketones into benzenediols

The Dakin oxidation (or Dakin reaction) is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde) or ketone reacts with hydrogen peroxide (H2O2) in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidised, whereas the H2O2 is reduced.

A diamine is an amine with exactly two amino groups. Diamines are used as monomers to prepare polyamides, polyimides, and polyureas. The term diamine refers mostly to primary diamines, as those are the most reactive.

<span class="mw-page-title-main">Cyclooctane</span> Chemical compound

Cyclooctane is a cycloalkane with the molecular formula (CH2)8. It is a simple colourless hydrocarbon, but it is often a reference compound for saturated eight-membered ring compounds in general.

The chemical substance 1,2-dioxetane is a heterocyclic, organic compound with formula C2O2H4, containing a ring of two adjacent oxygen atoms and two adjacent carbon atoms. It is therefore an organic peroxide, and can be viewed as a dimer of formaldehyde.

In organic chemistry, pentadiene is any hydrocarbon with an open chain of five carbons, connected by two single bonds and two double bonds. All those compounds have the same molecular formula C5H8. The inventory of pentadienes include:

<span class="mw-page-title-main">1,4-Dioxin</span> Chemical compound

1,4-Dioxin (also referred as dioxin or p-dioxin) is a heterocyclic, organic, non-aromatic compound with the chemical formula C4H4O2. There is an isomeric form of 1,4-dioxin, 1,2-dioxin (or o-dioxin). 1,2-Dioxin is very unstable due to its peroxide-like characteristics.

<span class="mw-page-title-main">Dioxirane</span> Chemical compound

In chemistry, dioxirane is an organic compound with formula CH
2
O
2
. The molecule consists of a ring with one methylene and two oxygen atoms. It is of interest as the smallest cyclic organic peroxide, but otherwise it is of little practical value.

<i>trans</i>-Cyclooctene Chemical compound

trans-Cyclooctene is a cyclic hydrocarbon with the formula [–(CH2)6CH=CH–], where the two C–C single bonds adjacent to the double bond are on opposite sides of the latter's plane. It is a colorless liquid with a disagreeable odor.

<span class="mw-page-title-main">Oxocarbon</span> Chemical compounds made of only carbon and oxygen

In chemistry, an oxocarbon or oxide of carbon is a chemical compound consisting only of carbon and oxygen. The simplest and most common oxocarbons are carbon monoxide (CO) and carbon dioxide. Many other stable or metastable oxides of carbon are known, but they are rarely encountered, such as carbon suboxide and mellitic anhydride.

<span class="mw-page-title-main">Xylylene</span>

In organic chemistry, a xylylene (sometimes quinone-dimethide) is any of the constitutional isomers having the formula C6H4(CH2)2. These compounds are related to the corresponding quinones and quinone methides by replacement of the oxygen atoms by CH2 groups. ortho- and para-xylylene are best known, although neither is stable in solid or liquid form. The meta form is a diradical. Certain substituted derivatives of xylylenes are however highly stable, such as tetracyanoquinodimethane and the xylylene dichlorides.

<span class="mw-page-title-main">1,2-Dioxolane</span> Chemical compound

1,2-Dioxolane is a chemical compound with formula C3H6O2, consisting of a ring of three carbon atoms and two oxygen atoms in adjacent positions. Its condensed structural formula is [–(CH
2
)3–O–O–]
.

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.