Oxepin: Difference between revisions

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 448773926

| ImageFileL1 = Oxepine.svg

| ImageSizeL1 = 110

| ImageAltL1 = Skeletal formula of oxepin

| ImageFileR1 = Oxepin-based-on-xtal-3D-bs-17.png

| ImageSizeR1 = 140

| ImageAltR1 = Ball-and-stick model of the oxepin molecule

| ImageFile2 = Oxepin-based-on-xtal-3D-bs-17-side-view.png

| ImageSize2 = 140

| PIN=Oxepine

| OtherNames=Oxacycloheptatriene

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=291-70-3

| PubChem=6451477

| SMILES=C1=CC=COC=C1

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = CVP5X85XX5

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4953942

| InChI = 1/C6H6O/c1-2-4-6-7-5-3-1/h1-6H

| InChIKey = ATYBXHSAIOKLMG-UHFFFAOYAS

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C6H6O/c1-2-4-6-7-5-3-1/h1-6H

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = ATYBXHSAIOKLMG-UHFFFAOYSA-N

|Section2={{Chembox Properties

| C=6 | H=6 | O=1

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

| Section8 = {{Chembox Related

| Related_ref =

| OtherFunction =

| OtherFunction_label =

| OtherCompounds = [[Cyclohexene oxide]]<br/>[[Oxonane]]

'''Oxepin''' is an [[oxygen]]-containing [[heterocycle]] consisting of a seven-membered [[ring (chemistry)|ring]] with three [[double bond]]s. The parent C₆H₆O exists as an [[chemical equilibrium|equilibrium]] mixture with '''benzene oxide'''.

[[File:Oxepin-benzene oxide.png|center|200px]]

The oxepin–benzene oxide equilibrium is affected by the ring [[substituent]]s.<ref name=TautHist /> A related dimethyl derivative exists mainly as the oxepin isomer, an orange liquid.<ref name=Me2Synth />

Oxepin is an intermediate in the oxidation of [[benzene]] by the [[cytochrome P450]] (CYP).<ref name=Tox /> Other [[arene oxide]]s are metabolites of the parent arene.

:[[File:Arenoxid Reaktionen.svg|360px|Formation and selected reactions of benzene oxide (2) and oxepin (3).]]

<references>

<ref name=Me2Synth>{{cite journal|title=2,7-Dimethyloxepin|first1=Leo&nbsp;A.|last1=Paquette |author1-link= Leo Paquette |first2=J.&nbsp;H. |last2=Barrett|journal=Org. Synth.|year=1969|volume=49|page=62|doi=10.15227/orgsyn.049.0062}}</ref>

<ref name=Tox>{{cite journal |doi=10.1289/ehp.93100293 |journal=Environmental Health Perspectives |title=The Toxicology of Benzene |volume=100 |pages=293–306 |first1=R.|last1=Snyder |first2= G. |last2=Witz |first3= B.&nbsp;D. |last3=Goldstein |year=1993 |pmc=1519582 |pmid=8354177|jstor=3431535 |doi-access=free }}</ref>

<ref name=TautHist>{{cite journal | doi = 10.1002/anie.196703851 | journal = Angewandte Chemie International Edition in English | title=Benzene Oxide–Oxepin Valence Tautomerism| volume=6 |issue=5 |pages =385–401 |first1=E.|last1=Vogel |first2=H.|last2=Günther | year = 1967}}</ref>

</references>

{{Commons category|Oxepin}}