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Article: Samarium(III) carbenoid as a competing reactive species in samarium-promoted cyclopropanation reactions

TitleSamarium(III) carbenoid as a competing reactive species in samarium-promoted cyclopropanation reactions
Authors
Wang, DZhao, CPhillips, DL
Issue Date2004
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2004, v. 69 n. 16, p. 5512-5515 How to Cite?
DOI: http://dx.doi.org/10.1021/jo0494679
AbstractThe trivalent samarium carbenoid I2SmCH2I-promoted cyclopropanation reactions with ethylene have been investigated and are predicted to be highly reactive, similarly to the divalent samarium carbenoid ISmCH2I. The methylene transfer and carbometalation pathways were explored and compared with and without coordination of THF solvent molecules to the carbenoid. The methylene transfer was found to be favored, with the barrier to reaction going from 12.9 to 9.2 kcal/mol compared to barriers of 15.4-17.5 kcal/mol for the carbometalation pathway upon the addition of one THF molecule.
Persistent Identifierhttp://hdl.handle.net/10722/69640
ISSN
0022-3263
2023 Impact Factor: 3.3
2023 SCImago Journal Rankings: 0.724
ISI Accession Number ID
WOS:000223008100055
References
References in Scopus

 

DC FieldValueLanguage
dc.contributor.authorWang, Den_HK
dc.contributor.authorZhao, Cen_HK
dc.contributor.authorPhillips, DLen_HK
dc.date.accessioned2010-09-06T06:15:30Z-
dc.date.available2010-09-06T06:15:30Z-
dc.date.issued2004en_HK
dc.identifier.citationJournal Of Organic Chemistry, 2004, v. 69 n. 16, p. 5512-5515en_HK
dc.identifier.issn0022-3263en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69640-
dc.description.abstractThe trivalent samarium carbenoid I2SmCH2I-promoted cyclopropanation reactions with ethylene have been investigated and are predicted to be highly reactive, similarly to the divalent samarium carbenoid ISmCH2I. The methylene transfer and carbometalation pathways were explored and compared with and without coordination of THF solvent molecules to the carbenoid. The methylene transfer was found to be favored, with the barrier to reaction going from 12.9 to 9.2 kcal/mol compared to barriers of 15.4-17.5 kcal/mol for the carbometalation pathway upon the addition of one THF molecule.en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jocen_HK
dc.relation.ispartofJournal of Organic Chemistryen_HK
dc.titleSamarium(III) carbenoid as a competing reactive species in samarium-promoted cyclopropanation reactionsen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0022-3263&volume=69&spage=5512&epage=5515&date=2004&atitle=Samarium(III)+carbenoid+as+a+competing+reactive+species+in+samarium-promoted+cyclopropanation+reactionsen_HK
dc.identifier.emailPhillips, DL:phillips@hku.hken_HK
dc.identifier.authorityPhillips, DL=rp00770en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/jo0494679en_HK
dc.identifier.scopuseid_2-s2.0-3543012555en_HK
dc.identifier.hkuros98491en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-3543012555&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume69en_HK
dc.identifier.issue16en_HK
dc.identifier.spage5512en_HK
dc.identifier.epage5515en_HK
dc.identifier.isiWOS:000223008100055-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridWang, D=7407071795en_HK
dc.identifier.scopusauthoridZhao, C=7403563836en_HK
dc.identifier.scopusauthoridPhillips, DL=7404519365en_HK
dc.identifier.issnl0022-3263-

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