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Article: Density functional study of selected mono-zinc and gem-dizinc radical carbenoid cyclopropanation reactions: observation of an efficient radical zinc carbenoid cyclopropanation reaction and the influence of the leaving group on ring closure

TitleDensity functional study of selected mono-zinc and gem-dizinc radical carbenoid cyclopropanation reactions: observation of an efficient radical zinc carbenoid cyclopropanation reaction and the influence of the leaving group on ring closure
Authors
KeywordsCarbenoid
Cyclopropanation
Density functional theory calculations
Radical
Zinc
Issue Date2003
PublisherWorld Scientific Publishing Co Pte Ltd. The Journal's web site is located at http://www.worldscinet.com/jtcc/jtcc.shtml
Citation
Journal of Theoretical and Computational Chemistry, 2003, v. 2 n. 3, p. 357-369 How to Cite?
AbstractWe report a theoretical study of the cyclopropanation reactions of EtZnCHI, (EtZn)2CH EtZnCHZnI, and EtZnCIZnI radicals with ethylene. The mono-zinc and gem-dizinc radical carbenoids can undergo cyclopropanation reactions with ethylene via a two-step reaction mechanism similar to that previously reported for the CH2I and IZnCH2 radicals. The barrier for the second reaction step (ring closure) was found to be highly dependent on the leaving group of the cyclopropanation reaction. In some cases, the (di)zinc carbenoid radical undergoes cyclopropanation via a low barrier of about 5–7 kcal/mol on the second reaction step and this is lower than the CH2I radical reaction which has a barrier of about 13.5 kcal/mol for the second reaction step. Our results suggest that in some cases, zinc radical carbenoid species have cyclopropanation reaction barriers that can be competitive with their related molecular Simmons-Smith carbenoid species reactions and produce somewhat different cyclopropanated products and leaving groups.
Persistent Identifierhttp://hdl.handle.net/10722/69843
ISSN
2015 Impact Factor: 0.619
2015 SCImago Journal Rankings: 0.251
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorZhao, Cen_HK
dc.contributor.authorWang, DQen_HK
dc.contributor.authorPhillips, DLen_HK
dc.date.accessioned2010-09-06T06:17:20Z-
dc.date.available2010-09-06T06:17:20Z-
dc.date.issued2003en_HK
dc.identifier.citationJournal of Theoretical and Computational Chemistry, 2003, v. 2 n. 3, p. 357-369en_HK
dc.identifier.issn0219-6336en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69843-
dc.description.abstractWe report a theoretical study of the cyclopropanation reactions of EtZnCHI, (EtZn)2CH EtZnCHZnI, and EtZnCIZnI radicals with ethylene. The mono-zinc and gem-dizinc radical carbenoids can undergo cyclopropanation reactions with ethylene via a two-step reaction mechanism similar to that previously reported for the CH2I and IZnCH2 radicals. The barrier for the second reaction step (ring closure) was found to be highly dependent on the leaving group of the cyclopropanation reaction. In some cases, the (di)zinc carbenoid radical undergoes cyclopropanation via a low barrier of about 5–7 kcal/mol on the second reaction step and this is lower than the CH2I radical reaction which has a barrier of about 13.5 kcal/mol for the second reaction step. Our results suggest that in some cases, zinc radical carbenoid species have cyclopropanation reaction barriers that can be competitive with their related molecular Simmons-Smith carbenoid species reactions and produce somewhat different cyclopropanated products and leaving groups.-
dc.languageengen_HK
dc.publisherWorld Scientific Publishing Co Pte Ltd. The Journal's web site is located at http://www.worldscinet.com/jtcc/jtcc.shtmlen_HK
dc.relation.ispartofJournal of Theoretical and Computational Chemistryen_HK
dc.rightsJournal of Theoretical and Computational Chemistry. Copyright © World Scientific Publishing Co Pte Ltd.-
dc.rightsFor preprints : Preprint of an article submitted for consideration in [Journal] © [Year] [copyright World Scientific Publishing Company] [Journal URL] For postprints : Electronic version of an article published as [Journal, Volume, Issue, Year, Pages] [Article DOI] © [copyright World Scientific Publishing Company] [Journal URL]-
dc.subjectCarbenoid-
dc.subjectCyclopropanation-
dc.subjectDensity functional theory calculations-
dc.subjectRadical-
dc.subjectZinc-
dc.titleDensity functional study of selected mono-zinc and gem-dizinc radical carbenoid cyclopropanation reactions: observation of an efficient radical zinc carbenoid cyclopropanation reaction and the influence of the leaving group on ring closureen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0219-6336&volume=2&issue=3&spage=357&epage=369&date=2003&atitle=Density+functional+study+of+selected+mono-zinc+and+gem-dizinc+radical+carbenoid+cyclopropanation+reactions:+observation+of+an+efficient+radical+zinc+carbenoid+cyclopropanation+reaction+and+the+influence+of+the+leaving+group+on+ring+closure+en_HK
dc.identifier.emailZhao, C: chzhaocy@yahoo.comen_HK
dc.identifier.emailPhillips, DL: phillips@hku.hken_HK
dc.identifier.authorityPhillips, DL=rp00770en_HK
dc.identifier.doi10.1142/S0219633603000549-
dc.identifier.hkuros92596en_HK
dc.identifier.volume2-
dc.identifier.issue3-
dc.identifier.spage357-
dc.identifier.epage369-
dc.identifier.isiWOS:000220867200005-
dc.publisher.placeSingapore-

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