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Article: Isopolyhalomethanes: Their formation, structures, properties and cyclopropanation reactions with olefins

TitleIsopolyhalomethanes: Their formation, structures, properties and cyclopropanation reactions with olefins
Authors
Issue Date2004
PublisherBentham Science Publishers Ltd. The Journal's web site is located at http://www.bentham.org/coc/index.htm
Citation
Current Organic Chemistry, 2004, v. 8 n. 9, p. 739-755 How to Cite?
AbstractAn overview of recent research on isopolyhalomethanes is presented that examines their formation, structure, properties and cyclopropanation reactions with olefins. Time-resolved experimental results show isopolyhalomethanes are formed vibrationally hot within a few picoseconds following solvent induced geminate recombination of the initially produced haloalkyl radical and halogen atom fragments of the parent polyhalomethane molecule photodissociation. The carbenoid behavior of the CH 2I-I isomer toward C=C bonds can be largely attributed to the CH 2I +I - radical ion pair character that activates the CH2 I moiety and the sp 2 bonding character of the C atom in the isopolyhalomethane species. Time-resolved resonance Raman and density functional theory studies on selected isopolyhalomethanes and their cyclopropanation reactions with olefins indicates the isopolyhalomethane lifetime and chemical reactivity relative to the intitially formed haloalkyl radical fragments helps to determine the efficiency of the isopolyhalomethane cyclopropanation reactions. The chemical reactivity of the CH 2I-I and the classic Simmons-Smith IZnCH 2I carbenoids towards olefins can be largely explained by their differing energetics for releasing the leaving group, steric demands and electrophilic character of the methylene group to be transferred. © 2004 Bentham Science Publishers Ltd.
Persistent Identifierhttp://hdl.handle.net/10722/70511
ISSN
2015 Impact Factor: 1.949
2015 SCImago Journal Rankings: 0.486
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorPhillips, DLen_HK
dc.contributor.authorFang, WHen_HK
dc.contributor.authorZheng, Xen_HK
dc.contributor.authorLi, YLen_HK
dc.contributor.authorWang, Den_HK
dc.contributor.authorKwok, WMen_HK
dc.date.accessioned2010-09-06T06:23:34Z-
dc.date.available2010-09-06T06:23:34Z-
dc.date.issued2004en_HK
dc.identifier.citationCurrent Organic Chemistry, 2004, v. 8 n. 9, p. 739-755en_HK
dc.identifier.issn1385-2728en_HK
dc.identifier.urihttp://hdl.handle.net/10722/70511-
dc.description.abstractAn overview of recent research on isopolyhalomethanes is presented that examines their formation, structure, properties and cyclopropanation reactions with olefins. Time-resolved experimental results show isopolyhalomethanes are formed vibrationally hot within a few picoseconds following solvent induced geminate recombination of the initially produced haloalkyl radical and halogen atom fragments of the parent polyhalomethane molecule photodissociation. The carbenoid behavior of the CH 2I-I isomer toward C=C bonds can be largely attributed to the CH 2I +I - radical ion pair character that activates the CH2 I moiety and the sp 2 bonding character of the C atom in the isopolyhalomethane species. Time-resolved resonance Raman and density functional theory studies on selected isopolyhalomethanes and their cyclopropanation reactions with olefins indicates the isopolyhalomethane lifetime and chemical reactivity relative to the intitially formed haloalkyl radical fragments helps to determine the efficiency of the isopolyhalomethane cyclopropanation reactions. The chemical reactivity of the CH 2I-I and the classic Simmons-Smith IZnCH 2I carbenoids towards olefins can be largely explained by their differing energetics for releasing the leaving group, steric demands and electrophilic character of the methylene group to be transferred. © 2004 Bentham Science Publishers Ltd.en_HK
dc.languageengen_HK
dc.publisherBentham Science Publishers Ltd. The Journal's web site is located at http://www.bentham.org/coc/index.htmen_HK
dc.relation.ispartofCurrent Organic Chemistryen_HK
dc.titleIsopolyhalomethanes: Their formation, structures, properties and cyclopropanation reactions with olefinsen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=1385-2728&volume=8&spage=739&epage=755&date=2004&atitle=Isopolyhalomethanes:+their+formation,+structures,+properties+and+cyclopropanation+reactions+with+olefinsen_HK
dc.identifier.emailPhillips, DL:phillips@hku.hken_HK
dc.identifier.authorityPhillips, DL=rp00770en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.2174/1385272043370483en_HK
dc.identifier.scopuseid_2-s2.0-2442484390en_HK
dc.identifier.hkuros90651en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-2442484390&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume8en_HK
dc.identifier.issue9en_HK
dc.identifier.spage739en_HK
dc.identifier.epage755en_HK
dc.identifier.isiWOS:000221362200001-
dc.publisher.placeNetherlandsen_HK
dc.identifier.scopusauthoridPhillips, DL=7404519365en_HK
dc.identifier.scopusauthoridFang, WH=7202236871en_HK
dc.identifier.scopusauthoridZheng, X=7404090253en_HK
dc.identifier.scopusauthoridLi, YL=24721643800en_HK
dc.identifier.scopusauthoridWang, D=24081882600en_HK
dc.identifier.scopusauthoridKwok, WM=7103129332en_HK

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