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styrene oxide : ウィキペディア英語版
styrene oxide

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Styrene oxide is an epoxide derived from styrene. It can be prepared by epoxidation of styrene with peroxybenzoic acid, in the Prilezhaev reaction:
Styrene oxide is slightly soluble in water. Trace amount of acid in water causes hydrolysis to racemic phenylethyleneglycol via aryl cation. If the amount of water is not sufficient, acid-catalyzed isomerization for phenylacetaldehyde will occur.〔(Verfahren zur Herstellung von Phenylacetaldehyden, BASF-Patent DE3546372A1 vom 2. Juli 1987 )〕
Styrene oxide in the body is metabolized to mandelic acid, phenyl glyoxylic acid, benzoic acid and hippuric acid.
== Stereospecific reaction ==
Since styrene oxide has a chiral center at the benzylic carbon atom, there are (''R'')-styrene oxide and (''S'')-styrene oxide. In addition, nucleophiles always attack the secondary carbon of the oxirane ring because of stability of the intermediate and steric hindrance. If optically pure reagent is used, only one optically pure compound will be obtained.

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