File Download

There are no files associated with this item.

  Links for fulltext
     (May Require Subscription)
Supplementary

Article: Novel cyclic ketones for catalytic oxidation reactions

TitleNovel cyclic ketones for catalytic oxidation reactions
Authors
Issue Date1998
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 1998, v. 63 n. 26, p. 9888-9894 How to Cite?
AbstractIn our effort to search for C2 symmetric and conformationally rigid chiral ketones as catalysts for asymmetric epoxidation, a series of cyclic ketones 4-10 were prepared from the corresponding diacids. Compared with acyclic ketones for epoxidation of trans-stilbene, those 9-, 10-, and 11- membered-ring cyclic ketones were found to have much higher catalytic activities, which were attributed to steric effects, electronic effects, and ring strains. By using the homogeneous acetonitrile-water solvent system, unfunctionalized olefins with various substitution patterns (with 5 mol % of ketone 9) and strongly electron-deficient olefins (with a 1:1 ketone 9:substrate ratio) were epoxidized with Oxone as terminal oxidant in 75-96% yield at room temperature and neutral pH. In addition, oxidation of alcohols (with 20 mol % of ketone 9) was carried out successfully with good isolated yields of aldehydes or ketones (75-88%).
Persistent Identifierhttp://hdl.handle.net/10722/68774
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.authorYip, YCen_HK
dc.contributor.authorTang, MWen_HK
dc.contributor.authorWong, MKen_HK
dc.contributor.authorCheung, KKen_HK
dc.date.accessioned2010-09-06T06:07:36Z-
dc.date.available2010-09-06T06:07:36Z-
dc.date.issued1998en_HK
dc.identifier.citationJournal Of Organic Chemistry, 1998, v. 63 n. 26, p. 9888-9894en_HK
dc.identifier.issn0022-3263en_HK
dc.identifier.urihttp://hdl.handle.net/10722/68774-
dc.description.abstractIn our effort to search for C2 symmetric and conformationally rigid chiral ketones as catalysts for asymmetric epoxidation, a series of cyclic ketones 4-10 were prepared from the corresponding diacids. Compared with acyclic ketones for epoxidation of trans-stilbene, those 9-, 10-, and 11- membered-ring cyclic ketones were found to have much higher catalytic activities, which were attributed to steric effects, electronic effects, and ring strains. By using the homogeneous acetonitrile-water solvent system, unfunctionalized olefins with various substitution patterns (with 5 mol % of ketone 9) and strongly electron-deficient olefins (with a 1:1 ketone 9:substrate ratio) were epoxidized with Oxone as terminal oxidant in 75-96% yield at room temperature and neutral pH. In addition, oxidation of alcohols (with 20 mol % of ketone 9) was carried out successfully with good isolated yields of aldehydes or ketones (75-88%).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.titleNovel cyclic ketones for catalytic oxidation reactionsen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0022-3263&volume=63&issue=26&spage=9888&epage=9894&date=1998&atitle=Novel+cyclic+ketones+for+catalytic+oxidation+reactionsen_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/jo981659een_HK
dc.identifier.scopuseid_2-s2.0-0032567328en_HK
dc.identifier.hkuros40136en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0032567328&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume63en_HK
dc.identifier.issue26en_HK
dc.identifier.spage9888en_HK
dc.identifier.epage9894en_HK
dc.identifier.isiWOS:000077834800049-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridYang, D=7404800756en_HK
dc.identifier.scopusauthoridYip, YC=7005596386en_HK
dc.identifier.scopusauthoridTang, MW=7401974042en_HK
dc.identifier.scopusauthoridWong, MK=7403908449en_HK
dc.identifier.scopusauthoridCheung, KK=7402406613en_HK

Export via OAI-PMH Interface in XML Formats


OR


Export to Other Non-XML Formats