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Article: Time-resolved resonance raman study of the reaction of isodiiodomethane with cyclohexene: Implications for the mechanism of photocyclopropanation of olefins using ultraviolet photolysis of diiodomethane

TitleTime-resolved resonance raman study of the reaction of isodiiodomethane with cyclohexene: Implications for the mechanism of photocyclopropanation of olefins using ultraviolet photolysis of diiodomethane
Authors
Issue Date2001
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jpca
Citation
Journal Of Physical Chemistry A, 2001, v. 105 n. 46, p. 10621-10625 How to Cite?
AbstractWe examine the chemical reaction of isodiiodomethane (CH2I-I) with cyclohexene using time-resolved resonance Raman spectroscopy. Our results indicate that CH2I-I reacts with cyclohexene to produce an iodine molecule leaving group on the 5-10 ns time scale which then almost immediately forms a I2:cyclohexene complex. This in conjunction with previous results from photochemistry experiments and recent density functional theory calculations indicates that isodiiodomethane is the methylene transfer agent mainly responsible for cyclopropanation of olefins when using ultraviolet photolysis of diiodomethane. We present a mechanism for photocyclopropanation that is consistent with both experimental and theoretical characterization of reaction intermediates and products formed after ultraviolet photolysis of diiodomethane in a condensed phase environment. We briefly discuss the differences and similarities in the behavior of the isodiiodomethane and the Simmons-Smith carbenoids toward cyclopropanation reactions with olefins. © 2001 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/70202
ISSN
2015 Impact Factor: 2.883
2015 SCImago Journal Rankings: 1.231
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorLi, YAen_HK
dc.contributor.authorLeung, KHen_HK
dc.contributor.authorPhillips, DLen_HK
dc.date.accessioned2010-09-06T06:20:40Z-
dc.date.available2010-09-06T06:20:40Z-
dc.date.issued2001en_HK
dc.identifier.citationJournal Of Physical Chemistry A, 2001, v. 105 n. 46, p. 10621-10625en_HK
dc.identifier.issn1089-5639en_HK
dc.identifier.urihttp://hdl.handle.net/10722/70202-
dc.description.abstractWe examine the chemical reaction of isodiiodomethane (CH2I-I) with cyclohexene using time-resolved resonance Raman spectroscopy. Our results indicate that CH2I-I reacts with cyclohexene to produce an iodine molecule leaving group on the 5-10 ns time scale which then almost immediately forms a I2:cyclohexene complex. This in conjunction with previous results from photochemistry experiments and recent density functional theory calculations indicates that isodiiodomethane is the methylene transfer agent mainly responsible for cyclopropanation of olefins when using ultraviolet photolysis of diiodomethane. We present a mechanism for photocyclopropanation that is consistent with both experimental and theoretical characterization of reaction intermediates and products formed after ultraviolet photolysis of diiodomethane in a condensed phase environment. We briefly discuss the differences and similarities in the behavior of the isodiiodomethane and the Simmons-Smith carbenoids toward cyclopropanation reactions with olefins. © 2001 American Chemical Society.en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jpcaen_HK
dc.relation.ispartofJournal of Physical Chemistry Aen_HK
dc.titleTime-resolved resonance raman study of the reaction of isodiiodomethane with cyclohexene: Implications for the mechanism of photocyclopropanation of olefins using ultraviolet photolysis of diiodomethaneen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=1089-5639&volume=105&issue=46&spage=10621&epage=10625&date=2001&atitle=Time-resolved+resonance+raman+study+of+the+reaction+of+isodiiodomethane+with+cyclohexene:++implications+for+the+mechanism+of+photocyclopropanation+of+olefins+using+ultraviolet+photolysis+of+diiodomethaneen_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/jp0128527-
dc.identifier.scopuseid_2-s2.0-0035936233en_HK
dc.identifier.hkuros73870en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0035936233&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume105en_HK
dc.identifier.issue46en_HK
dc.identifier.spage10621en_HK
dc.identifier.epage10625en_HK
dc.identifier.isiWOS:000172465900018-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridLi, YA=27168456500en_HK
dc.identifier.scopusauthoridLeung, KH=7401860609en_HK
dc.identifier.scopusauthoridPhillips, DL=7404519365en_HK

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