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Article: Stereochemistry of the spontaneous, acid-catalyzed and base-catalyzed hydrolyses of styrene oxide

TitleStereochemistry of the spontaneous, acid-catalyzed and base-catalyzed hydrolyses of styrene oxide
Authors
Issue Date1994
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal of Organic Chemistry, 1994, v. 59 n. 7, p. 1638-1641 How to Cite?
AbstractThe stereochemical courses of the spontaneous, hydronium ion-catalyzed and hydroxide ion-catalyzed hydrolyses of (R)-styrene oxide have been determined by 1H NMR analysis of the bis-(+)-α-(methoxy-α-trifluoromethyl)phenylacetate diesters of the styrene glycol products from each reaction. The glycol product from the spontaneous reaction of chiral styrene oxide is the result of 93% inversion and 7% retention. This result, coupled with published results of 18O-labeling experiments, indicates that essentially all of the styrene oxide that reacts with cleavage of the benzyl C-O bond yields glycol with inversion of stereochemistry at the benzyl carbon. A mechanism involving addition of neutral water concerted with benzyl C-O bond breaking is proposed for this reaction. The glycol product from the acid-catalyzed reaction was determined to be the result of 67% inversion and 33 % retention at the benzyl carbon. This result, which agrees with one previous publication and contradicts that of another, reflects the stereochemistry of addition of solvent to the benzyl carbon. Consistent with a recent report that 18O-hydroxide attacks the α- and β-carbons of styrene oxide at almost equal rates, styrene glycol from the reaction of chiral styrene oxide with sodium hydroxide was found to be, within experimental error, completely racemic. © 1994 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/90923
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095

 

DC FieldValueLanguage
dc.contributor.authorLin, Ben_HK
dc.contributor.authorWhalen, DLen_HK
dc.date.accessioned2010-09-17T10:10:24Z-
dc.date.available2010-09-17T10:10:24Z-
dc.date.issued1994en_HK
dc.identifier.citationJournal of Organic Chemistry, 1994, v. 59 n. 7, p. 1638-1641en_HK
dc.identifier.issn0022-3263en_HK
dc.identifier.urihttp://hdl.handle.net/10722/90923-
dc.description.abstractThe stereochemical courses of the spontaneous, hydronium ion-catalyzed and hydroxide ion-catalyzed hydrolyses of (R)-styrene oxide have been determined by 1H NMR analysis of the bis-(+)-α-(methoxy-α-trifluoromethyl)phenylacetate diesters of the styrene glycol products from each reaction. The glycol product from the spontaneous reaction of chiral styrene oxide is the result of 93% inversion and 7% retention. This result, coupled with published results of 18O-labeling experiments, indicates that essentially all of the styrene oxide that reacts with cleavage of the benzyl C-O bond yields glycol with inversion of stereochemistry at the benzyl carbon. A mechanism involving addition of neutral water concerted with benzyl C-O bond breaking is proposed for this reaction. The glycol product from the acid-catalyzed reaction was determined to be the result of 67% inversion and 33 % retention at the benzyl carbon. This result, which agrees with one previous publication and contradicts that of another, reflects the stereochemistry of addition of solvent to the benzyl carbon. Consistent with a recent report that 18O-hydroxide attacks the α- and β-carbons of styrene oxide at almost equal rates, styrene glycol from the reaction of chiral styrene oxide with sodium hydroxide was found to be, within experimental error, completely racemic. © 1994 American Chemical Society.en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jocen_HK
dc.relation.ispartofJournal of Organic Chemistryen_HK
dc.titleStereochemistry of the spontaneous, acid-catalyzed and base-catalyzed hydrolyses of styrene oxideen_HK
dc.typeArticleen_HK
dc.identifier.emailLin, B:blin@hku.hken_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.scopuseid_2-s2.0-0000714513en_HK
dc.identifier.volume59en_HK
dc.identifier.issue7en_HK
dc.identifier.spage1638en_HK
dc.identifier.epage1641en_HK

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