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Article: Preparation and reactivities of chiral manganese(III) and copper(II) complexes of binaphthyl Schiff bases

TitlePreparation and reactivities of chiral manganese(III) and copper(II) complexes of binaphthyl Schiff bases
Authors
Issue Date1996
PublisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/dalton
Citation
Journal Of The Chemical Society - Dalton Transactions, 1996 n. 4, p. 405-414 How to Cite?
AbstractA series of chiral Schiff bases, 2,2′-bis(3-R 1-5-R 2-2-hydroxybenzylideneamino)-1,1′-binaphthyl H 2L (R 2 = Cl, R 1 = Cl, Me, Et or NO 2; R 2 = Me, R 1 = Bu t; R 2 = NO 2, R 1 = H, Me, Et, Pr i, Bu t or Cl), and their complexes [CuL 1] 1 and [Mn 2L 1 2(OMe) 2] 2 (R 1 = R 2 = Cl) have been prepared. The crystal structure of the racemic form of 1 has been determined. Complex 1 is an active catalyst for the oxidation of alkenes by tertbutyl hydroperoxide. On the contrary, 2 is inert towards alkene epoxidation by PhIO. However, upon mixing Mn(O 2CMe) 3·xH 2O and H 2L in acetonitrile a green solution was obtained which could effect asymmetric epoxidation of alkenes by PhIO. The effects of the steric and electronic effects of the R 1 and R 2 substituents, temperature, and the addition of donors like N-methyl- and 2-methyl-imidazole and pyridine N-oxide on the catalytic activity of the Mn III + (S)-H 2L systems towards alkene epoxidation have been investigated. When R 1 = Et and R 2 = NO 2 the best enantiomeric excesses of 58 and 43% were found for epoxidation of cis-β-methylstyrene to (1S,2R)-cis-β-methylstyrene oxide and 4-chlorostyrene to 4-(S)-chlorostyrene oxide respectively.
Persistent Identifierhttp://hdl.handle.net/10722/69331
ISSN
1999 Impact Factor: 2.31
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorHo, CWen_HK
dc.contributor.authorCheng, WCen_HK
dc.contributor.authorCheng, MCen_HK
dc.contributor.authorPeng, SMen_HK
dc.contributor.authorCheng, KFen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2010-09-06T06:12:41Z-
dc.date.available2010-09-06T06:12:41Z-
dc.date.issued1996en_HK
dc.identifier.citationJournal Of The Chemical Society - Dalton Transactions, 1996 n. 4, p. 405-414en_HK
dc.identifier.issn0300-9246en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69331-
dc.description.abstractA series of chiral Schiff bases, 2,2′-bis(3-R 1-5-R 2-2-hydroxybenzylideneamino)-1,1′-binaphthyl H 2L (R 2 = Cl, R 1 = Cl, Me, Et or NO 2; R 2 = Me, R 1 = Bu t; R 2 = NO 2, R 1 = H, Me, Et, Pr i, Bu t or Cl), and their complexes [CuL 1] 1 and [Mn 2L 1 2(OMe) 2] 2 (R 1 = R 2 = Cl) have been prepared. The crystal structure of the racemic form of 1 has been determined. Complex 1 is an active catalyst for the oxidation of alkenes by tertbutyl hydroperoxide. On the contrary, 2 is inert towards alkene epoxidation by PhIO. However, upon mixing Mn(O 2CMe) 3·xH 2O and H 2L in acetonitrile a green solution was obtained which could effect asymmetric epoxidation of alkenes by PhIO. The effects of the steric and electronic effects of the R 1 and R 2 substituents, temperature, and the addition of donors like N-methyl- and 2-methyl-imidazole and pyridine N-oxide on the catalytic activity of the Mn III + (S)-H 2L systems towards alkene epoxidation have been investigated. When R 1 = Et and R 2 = NO 2 the best enantiomeric excesses of 58 and 43% were found for epoxidation of cis-β-methylstyrene to (1S,2R)-cis-β-methylstyrene oxide and 4-chlorostyrene to 4-(S)-chlorostyrene oxide respectively.en_HK
dc.languageengen_HK
dc.publisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/daltonen_HK
dc.relation.ispartofJournal of the Chemical Society - Dalton Transactionsen_HK
dc.titlePreparation and reactivities of chiral manganese(III) and copper(II) complexes of binaphthyl Schiff basesen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=1472-7773&volume=&spage=405&epage=414&date=1996&atitle=Preparation+and+reactivities+of+chiral+manganese(III)+and+copper(II)+complexes+of+binaphthyl+Schiff+basesen_HK
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1039/DT9960000405-
dc.identifier.scopuseid_2-s2.0-33748479238en_HK
dc.identifier.hkuros21688en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-33748479238&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.issue4en_HK
dc.identifier.spage405en_HK
dc.identifier.epage414en_HK
dc.identifier.isiWOS:A1996TW35100001-
dc.identifier.scopusauthoridHo, CW=55222468200en_HK
dc.identifier.scopusauthoridCheng, WC=7402169293en_HK
dc.identifier.scopusauthoridCheng, MC=36833891700en_HK
dc.identifier.scopusauthoridPeng, SM=35464852200en_HK
dc.identifier.scopusauthoridCheng, KF=7402997838en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK

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