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Article: Regioselective intramolecular oxidation of phenols and anisoles by dioxiranes generated in situ

TitleRegioselective intramolecular oxidation of phenols and anisoles by dioxiranes generated in situ
Authors
Issue Date2000
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2000, v. 65 n. 13, p. 4179-4184 How to Cite?
AbstractA novel method for regioselective oxidation of phenols and anisoles has been developed in which dioxiranes, generated in situ from ketones and Oxone, oxidize phenol derivatives in an intramolecular fashion. A series of ketones with electron-withdrawing groups, such as CF 3COOMe, and CH 2Cl, were attached to phenols, anisoles, or aryl rings via a C 2 or C 3 methylene linker. In a homogeneous solvent system of CH 3CN and H 2O, oxidation of phenol derivatives 1-10 afforded spiro 2-hydroxydienones in 24-55% yields regardless of the presence of other substituents (ortho Me, meta Me or Br) on the aryl ring and the length of the linker. Experimental evidences were provided to support the mechanism that involves a regioselective π bond epoxidation of aryl rings followed by epoxide rearrangement and hemiketal formation.
Persistent Identifierhttp://hdl.handle.net/10722/69240
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorYang, Den_HK
dc.contributor.authorWong, MKen_HK
dc.contributor.authorYan, Zen_HK
dc.date.accessioned2010-09-06T06:11:51Z-
dc.date.available2010-09-06T06:11:51Z-
dc.date.issued2000en_HK
dc.identifier.citationJournal Of Organic Chemistry, 2000, v. 65 n. 13, p. 4179-4184en_HK
dc.identifier.issn0022-3263en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69240-
dc.description.abstractA novel method for regioselective oxidation of phenols and anisoles has been developed in which dioxiranes, generated in situ from ketones and Oxone, oxidize phenol derivatives in an intramolecular fashion. A series of ketones with electron-withdrawing groups, such as CF 3COOMe, and CH 2Cl, were attached to phenols, anisoles, or aryl rings via a C 2 or C 3 methylene linker. In a homogeneous solvent system of CH 3CN and H 2O, oxidation of phenol derivatives 1-10 afforded spiro 2-hydroxydienones in 24-55% yields regardless of the presence of other substituents (ortho Me, meta Me or Br) on the aryl ring and the length of the linker. Experimental evidences were provided to support the mechanism that involves a regioselective π bond epoxidation of aryl rings followed by epoxide rearrangement and hemiketal formation.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.titleRegioselective intramolecular oxidation of phenols and anisoles by dioxiranes generated in situen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0022-3263&volume=65&spage=4179&epage=4184&date=2000&atitle=Regioselective+intramolecular+oxidation+of+phenols+and+anisoles+by+dioxiranes+generated+in+situen_HK
dc.identifier.emailYang, D:yangdan@hku.hken_HK
dc.identifier.authorityYang, D=rp00825en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/jo000458jen_HK
dc.identifier.scopuseid_2-s2.0-0034733112en_HK
dc.identifier.hkuros50328en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0034733112&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume65en_HK
dc.identifier.issue13en_HK
dc.identifier.spage4179en_HK
dc.identifier.epage4184en_HK
dc.identifier.isiWOS:000087925800035-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridYang, D=7404800756en_HK
dc.identifier.scopusauthoridWong, MK=37105480700en_HK
dc.identifier.scopusauthoridYan, Z=7402519416en_HK

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