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Article: Remarkably stable iron porphyrins bearing nonheteroatom-stabilized carbene or (alkoxycarbonyl)carbenes: Isolation, X-ray crystal structures, and carbon atom transfer reactions with hydrocarbons

TitleRemarkably stable iron porphyrins bearing nonheteroatom-stabilized carbene or (alkoxycarbonyl)carbenes: Isolation, X-ray crystal structures, and carbon atom transfer reactions with hydrocarbons
Authors
Issue Date2002
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, 2002, v. 124 n. 44, p. 13185-13193 How to Cite?
AbstractReactions of [Fe(TPFPP)] (TPFPP = meso-tetrakis(pentafluorophenyl)porphyrinato dianion) with diazo compounds N 2C(Ph)R (R = Ph, CO 2Et, CO 2CH 2CH=CH 2) afforded [Fe(TPFPP)(C(Ph)R)] (R = Ph (1), CO 2Et (2), CO 2CH 2CH=CH 2 (3)) in 65-70% yields. Treatment of 1 with N-methylimidazole (Melm) gave the adduct [Fe(TPFPP)(CPh 2)(Melm)] (4) in 65% yield. These new iron porphyrin carbene complexes were characterized by NMR and UV-vis spectroscopy, mass spectrometry, and elemental analyses. X-ray crystal structure determinations of 1·0.5C 6H 6·0.5CH 2Cl 2 and 4 reveal Fe=CPh 2 bond lengths of 1.767(3) (1) and 1.827(5) Å (4), together with large ruffling distortions of the TPFPP macrocycle. Complexes 2 and 4 are reactive toward styrene, affording the corresponding cyclopropanes in 82 and 53% yields, respectively. Complex 1 is an active catalyst for both intermolecular cyclopropanation of styrenes with ethyl diazoacetate and intramolecular cyclopropanation of allylic diazoacetates. Reactions of 2 and 4 with cyclohexene or cumene produced allylic or benzylic C-H insertion products in up to 83% yield.
Persistent Identifierhttp://hdl.handle.net/10722/69891
ISSN
2015 Impact Factor: 13.038
2015 SCImago Journal Rankings: 7.123
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorLi, Yen_HK
dc.contributor.authorHuang, JSen_HK
dc.contributor.authorZhou, ZYen_HK
dc.contributor.authorChe, CMen_HK
dc.contributor.authorYou, XZen_HK
dc.date.accessioned2010-09-06T06:17:47Z-
dc.date.available2010-09-06T06:17:47Z-
dc.date.issued2002en_HK
dc.identifier.citationJournal Of The American Chemical Society, 2002, v. 124 n. 44, p. 13185-13193en_HK
dc.identifier.issn0002-7863en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69891-
dc.description.abstractReactions of [Fe(TPFPP)] (TPFPP = meso-tetrakis(pentafluorophenyl)porphyrinato dianion) with diazo compounds N 2C(Ph)R (R = Ph, CO 2Et, CO 2CH 2CH=CH 2) afforded [Fe(TPFPP)(C(Ph)R)] (R = Ph (1), CO 2Et (2), CO 2CH 2CH=CH 2 (3)) in 65-70% yields. Treatment of 1 with N-methylimidazole (Melm) gave the adduct [Fe(TPFPP)(CPh 2)(Melm)] (4) in 65% yield. These new iron porphyrin carbene complexes were characterized by NMR and UV-vis spectroscopy, mass spectrometry, and elemental analyses. X-ray crystal structure determinations of 1·0.5C 6H 6·0.5CH 2Cl 2 and 4 reveal Fe=CPh 2 bond lengths of 1.767(3) (1) and 1.827(5) Å (4), together with large ruffling distortions of the TPFPP macrocycle. Complexes 2 and 4 are reactive toward styrene, affording the corresponding cyclopropanes in 82 and 53% yields, respectively. Complex 1 is an active catalyst for both intermolecular cyclopropanation of styrenes with ethyl diazoacetate and intramolecular cyclopropanation of allylic diazoacetates. Reactions of 2 and 4 with cyclohexene or cumene produced allylic or benzylic C-H insertion products in up to 83% yield.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.titleRemarkably stable iron porphyrins bearing nonheteroatom-stabilized carbene or (alkoxycarbonyl)carbenes: Isolation, X-ray crystal structures, and carbon atom transfer reactions with hydrocarbonsen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0002-7863&volume=124&issue=44&spage=13185&epage=13193&date=2002&atitle=Remarkably+stable+iron+porphyrins+bearing+nonheteroatom-stabilized+carbene+or+(alkoxycarbonyl)carbenes;++Isolation,+X-ray+crystal+structures,+and+carbon+atom+transfer+reactions+with+hydrocarbonsen_HK
dc.identifier.emailHuang, JS:jshuang@hkucc.hku.hken_HK
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.authorityHuang, JS=rp00709en_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ja020391cen_HK
dc.identifier.pmid12405847-
dc.identifier.scopuseid_2-s2.0-0037032218en_HK
dc.identifier.hkuros81067en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0037032218&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume124en_HK
dc.identifier.issue44en_HK
dc.identifier.spage13185en_HK
dc.identifier.epage13193en_HK
dc.identifier.isiWOS:000178966700047-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridLi, Y=35187394200en_HK
dc.identifier.scopusauthoridHuang, JS=7407192639en_HK
dc.identifier.scopusauthoridZhou, ZY=35081598000en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK
dc.identifier.scopusauthoridYou, XZ=36072101800en_HK

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