| 词条 | Arene oxide |
| 释义 |
In chemistry, an arene oxide is an epoxide of an arene. Two important families of arene oxides are benzene oxides and naphthalene oxides as these are intermediates in the oxidative degradation of benzene and naphthalene, two common pollutants.[1] Benzopyrene is also converted to an epoxide, (+)-benzo[a]pyrene-7,8-epoxide. Selected reactionsBenzene oxide (C6H6O) exists as an equilibrium mixture with the seven-membered ring oxepin three double bonds. They are valence isomers.[2] Arene oxides are highly reactive. Benzene oxide and naphthalene-1,2-oxide hydrate to give dihydroxydihydrobenzene and 1,2-dihydroxydihydronaphthalene, respectively. The hydration is catalyzed by epoxide hydrolase enzymes. Dehydration of these diols, which is driven by rearomatization, gives phenol and 1-naphthol. Oxidation of 1,2-dihydroxydihydronaphthalene, catalyzed by dihydrodiol dehydrogenase, gives the 1,2-naphthoquinone.[3] References1. ^{{cite journal | vauthors = Snyder R, Witz G, Goldstein BD | title = The toxicology of benzene | journal = Environ. Health Perspect. | volume = 100 | issue = | pages = 293–306 | date = April 1993 | pmid = 8354177 | pmc = 1519582 | doi = 10.1289/ehp.93100293 }} 2. ^{{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 |vauthors = Vogel E, Günther H | year = 1967}} 3. ^{{cite journal | vauthors = Kumagai Y, Shinkai Y, Miura T, Cho AK | title = The chemical biology of naphthoquinones and its environmental implications | journal = Annu. Rev. Pharmacol. Toxicol. | volume = 52 | issue = | pages = 221–47 | date = 2012 | pmid = 21942631 | doi = 10.1146/annurev-pharmtox-010611-134517 }} 3 : Oxepines|Human metabolites|Epoxides |
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