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Article: Density functional theory investigation of the reactivity of LiCH2I and lodomethylzinc phenoxide cyclopropanation reagents with olefins

TitleDensity functional theory investigation of the reactivity of LiCH2I and lodomethylzinc phenoxide cyclopropanation reagents with olefins
Authors
Wang, DPhillips, DLFang, WH
Issue Date2002
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/organometallics
Citation
Organometallics, 2002, v. 21 n. 26, p. 5901-5910 How to Cite?
DOI: http://dx.doi.org/10.1021/om020679a
AbstractWe report a systematic density functional theory investigation for the reactions of LiCH2I, IZnCH2I, iodomethylzinc phenoxide (PhOZnCH2I), 2,4,6-F3-PhOZnCH2I, and 2,4,6-Cl3PhOZnCH2I with CH2CH2, trans-CH3CHCHCH3, and PhCHCH2. All of the reactions examined displayed similar concerted mechanisms for the cyclopropanation of these reagents. The zinc carbenoids had similar barriers for the cyclopropanation reaction (in the 17-21 kcal/mol range), while the LiCH2I carbenoid had a much lower barrier for the cyclopropanation reactions (in the 6-7 kcal/mol range). The properties and chemical reactivity of the carbenoids investigated here were compared to each other and to recent results for the isodiiodomethane (CH2I-I) species.
Persistent Identifierhttp://hdl.handle.net/10722/167411
ISSN
0276-7333
2023 Impact Factor: 2.5
2023 SCImago Journal Rankings: 0.654
ISI Accession Number ID
WOS:000179932500026
References
References in Scopus

 

DC FieldValueLanguage
dc.contributor.authorWang, Den_US
dc.contributor.authorPhillips, DLen_US
dc.contributor.authorFang, WHen_US
dc.date.accessioned2012-10-08T03:06:40Z-
dc.date.available2012-10-08T03:06:40Z-
dc.date.issued2002en_US
dc.identifier.citationOrganometallics, 2002, v. 21 n. 26, p. 5901-5910en_US
dc.identifier.issn0276-7333en_US
dc.identifier.urihttp://hdl.handle.net/10722/167411-
dc.description.abstractWe report a systematic density functional theory investigation for the reactions of LiCH2I, IZnCH2I, iodomethylzinc phenoxide (PhOZnCH2I), 2,4,6-F3-PhOZnCH2I, and 2,4,6-Cl3PhOZnCH2I with CH2CH2, trans-CH3CHCHCH3, and PhCHCH2. All of the reactions examined displayed similar concerted mechanisms for the cyclopropanation of these reagents. The zinc carbenoids had similar barriers for the cyclopropanation reaction (in the 17-21 kcal/mol range), while the LiCH2I carbenoid had a much lower barrier for the cyclopropanation reactions (in the 6-7 kcal/mol range). The properties and chemical reactivity of the carbenoids investigated here were compared to each other and to recent results for the isodiiodomethane (CH2I-I) species.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/organometallicsen_US
dc.relation.ispartofOrganometallicsen_US
dc.titleDensity functional theory investigation of the reactivity of LiCH2I and lodomethylzinc phenoxide cyclopropanation reagents with olefinsen_US
dc.typeArticleen_US
dc.identifier.emailPhillips, DL:phillips@hku.hken_US
dc.identifier.authorityPhillips, DL=rp00770en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/om020679aen_US
dc.identifier.scopuseid_2-s2.0-0013350854en_US
dc.identifier.hkuros77119-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0013350854&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume21en_US
dc.identifier.issue26en_US
dc.identifier.spage5901en_US
dc.identifier.epage5910en_US
dc.identifier.isiWOS:000179932500026-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridWang, D=7407071795en_US
dc.identifier.scopusauthoridPhillips, DL=7404519365en_US
dc.identifier.scopusauthoridFang, WH=7202236871en_US
dc.identifier.issnl0276-7333-

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