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Article: Time-resolved resonance Raman and density functional study of an azirine intermediate in the 2-fluorenylnitrene ring-expansion reaction to form a dehydroazepine product

TitleTime-resolved resonance Raman and density functional study of an azirine intermediate in the 2-fluorenylnitrene ring-expansion reaction to form a dehydroazepine product
Authors
Issue Date2003
PublisherWiley - VCH Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistry
Citation
Chemistry - A European Journal, 2003, v. 9 n. 6, p. 1377-1386 How to Cite?
AbstractWe report time-resolved resonance Raman spectra for the azirine intermediate produced in the 2-fluorenylnitrene ring-expansion reaction to form a dehydroazepine product. The Raman bands obtained with a 252.7 nm probe wavelength and 500 ns delay time exhibit reasonable agreement with predicted vibrational frequencies from density functional calculations for two isomers of azirine intermediates that may be formed from a 2-fluorenylnitrene precursor. The Raman bands observed for delay times of 15 ns and 10 μs were consistent with predicted vibrational frequencies from density functional calculations for the 2-fluorenylnitrene and dehydroazepine product species as well as previously reported 416 nm time-resolved Raman spectra obtained on the ns and μs time scales. Our results demonstrate that the 2-fluorenylnitrene ring-expansion reaction to produce dehydroazepine products proceeds via relatively long-lived 2-fluorenylnitrene and azirine intermediates. Substitution of a phenyl ring para to the nitrene group of phenylnitrene appears to lead to significant changes in the ring-expansion reaction so that longer lived arylnitrene and azirine intermediates can be observed. This should enable the chemical reactivity of azirine intermediates formed from arylnitrenes to be examined more readily.
Persistent Identifierhttp://hdl.handle.net/10722/167789
ISSN
2015 Impact Factor: 5.771
2015 SCImago Journal Rankings: 2.323
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorOng, SYen_US
dc.contributor.authorZhu, Pen_US
dc.contributor.authorLeung, KHen_US
dc.contributor.authorPhillips, DLen_US
dc.date.accessioned2012-10-08T03:11:37Z-
dc.date.available2012-10-08T03:11:37Z-
dc.date.issued2003en_US
dc.identifier.citationChemistry - A European Journal, 2003, v. 9 n. 6, p. 1377-1386en_US
dc.identifier.issn0947-6539en_US
dc.identifier.urihttp://hdl.handle.net/10722/167789-
dc.description.abstractWe report time-resolved resonance Raman spectra for the azirine intermediate produced in the 2-fluorenylnitrene ring-expansion reaction to form a dehydroazepine product. The Raman bands obtained with a 252.7 nm probe wavelength and 500 ns delay time exhibit reasonable agreement with predicted vibrational frequencies from density functional calculations for two isomers of azirine intermediates that may be formed from a 2-fluorenylnitrene precursor. The Raman bands observed for delay times of 15 ns and 10 μs were consistent with predicted vibrational frequencies from density functional calculations for the 2-fluorenylnitrene and dehydroazepine product species as well as previously reported 416 nm time-resolved Raman spectra obtained on the ns and μs time scales. Our results demonstrate that the 2-fluorenylnitrene ring-expansion reaction to produce dehydroazepine products proceeds via relatively long-lived 2-fluorenylnitrene and azirine intermediates. Substitution of a phenyl ring para to the nitrene group of phenylnitrene appears to lead to significant changes in the ring-expansion reaction so that longer lived arylnitrene and azirine intermediates can be observed. This should enable the chemical reactivity of azirine intermediates formed from arylnitrenes to be examined more readily.en_US
dc.languageengen_US
dc.publisherWiley - VCH Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistryen_US
dc.relation.ispartofChemistry - A European Journalen_US
dc.titleTime-resolved resonance Raman and density functional study of an azirine intermediate in the 2-fluorenylnitrene ring-expansion reaction to form a dehydroazepine producten_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.doi10.1002/chem.200390157en_US
dc.identifier.pmid12645027-
dc.identifier.scopuseid_2-s2.0-0037451478en_US
dc.identifier.hkuros81034-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0037451478&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume9en_US
dc.identifier.issue6en_US
dc.identifier.spage1377en_US
dc.identifier.epage1386en_US
dc.identifier.isiWOS:000181817400014-
dc.publisher.placeGermanyen_US
dc.identifier.scopusauthoridOng, SY=7202336462en_US
dc.identifier.scopusauthoridZhu, P=7202169049en_US
dc.identifier.scopusauthoridLeung, KH=7401860609en_US
dc.identifier.scopusauthoridPhillips, DL=7404519365en_US

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