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Article: A novel epoxidation reaction of olefins using a combination of chloramine-M, benzaldehyde, and benzyltriethylammonium chloride

TitleA novel epoxidation reaction of olefins using a combination of chloramine-M, benzaldehyde, and benzyltriethylammonium chloride
Authors
Yang, DZhang, CWang, XC
Issue Date2000
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html
Citation
Journal Of The American Chemical Society, 2000, v. 122 n. 17, p. 4039-4043 How to Cite?
DOI: http://dx.doi.org/10.1021/ja993472q
AbstractA combination of Chloramine-M (CH3SO2NClNa), benzaldehyde, and benzyltriethylammonium chloride (BTEAC) was found to epoxidize a wide range of olefins. While epoxidation of trans-olefins provided exclusively trans- epoxides, cis-olefins (cis-stilbene, cis-β-methylstyrene, and 4-cis-octene) gave trans-epoxides as major products. Good to excellent diastereoselectivities were obtained for epoxidation of two substituted cyclohexenes. Chloramine-T was found to give a slower reaction than Chloramine-M. cis-N-Sulfonyloxaziridine D is proposed to be the epoxidizing agent in this novel epoxidation reaction on the basis of the mechanistic studies.
Persistent Identifierhttp://hdl.handle.net/10722/69645
ISSN
0002-7863
2023 Impact Factor: 14.4
2023 SCImago Journal Rankings: 5.489
ISI Accession Number ID
WOS:000086950500008
References
References in Scopus

 

DC FieldValueLanguage
dc.contributor.authorYang, Den_HK
dc.contributor.authorZhang, Cen_HK
dc.contributor.authorWang, XCen_HK
dc.date.accessioned2010-09-06T06:15:33Z-
dc.date.available2010-09-06T06:15:33Z-
dc.date.issued2000en_HK
dc.identifier.citationJournal Of The American Chemical Society, 2000, v. 122 n. 17, p. 4039-4043en_HK
dc.identifier.issn0002-7863en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69645-
dc.description.abstractA combination of Chloramine-M (CH3SO2NClNa), benzaldehyde, and benzyltriethylammonium chloride (BTEAC) was found to epoxidize a wide range of olefins. While epoxidation of trans-olefins provided exclusively trans- epoxides, cis-olefins (cis-stilbene, cis-β-methylstyrene, and 4-cis-octene) gave trans-epoxides as major products. Good to excellent diastereoselectivities were obtained for epoxidation of two substituted cyclohexenes. Chloramine-T was found to give a slower reaction than Chloramine-M. cis-N-Sulfonyloxaziridine D is proposed to be the epoxidizing agent in this novel epoxidation reaction on the basis of the mechanistic studies.en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.htmlen_HK
dc.relation.ispartofJournal of the American Chemical Societyen_HK
dc.titleA novel epoxidation reaction of olefins using a combination of chloramine-M, benzaldehyde, and benzyltriethylammonium chlorideen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0002-7863&volume=122&issue=17&spage=4039&epage=4043&date=2000&atitle=A+novel+epoxidation+reaction+of+olefins+using+a+combination+of+chloramine-M,+benzaldehyde,+and+benzyltriethylammonium+chlorideen_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/ja993472qen_HK
dc.identifier.scopuseid_2-s2.0-0034600252en_HK
dc.identifier.hkuros49897en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0034600252&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume122en_HK
dc.identifier.issue17en_HK
dc.identifier.spage4039en_HK
dc.identifier.epage4043en_HK
dc.identifier.isiWOS:000086950500008-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridYang, D=7404800756en_HK
dc.identifier.scopusauthoridZhang, C=7405494641en_HK
dc.identifier.scopusauthoridWang, XC=9744761800en_HK
dc.identifier.issnl0002-7863-

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