In
chemistry, an
arene oxide is an
epoxide of an
arene. Two important families of arene oxides are
and naphthalene oxides as these are intermediates in the oxidative degradation of
benzene and
naphthalene, two common
.
is also converted to an epoxide, (+)-benzo
apyrene-7,8-epoxide.
Selected reactions
Benzene oxide (C
6H
6O) exists as an equilibrium mixture with the seven-membered ring
oxepin, which has three
. They are
and in equilibrium via disrotatory 6π ring closing and opening.
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.
