File Download

There are no files associated with this item.

  Links for fulltext
     (May Require Subscription)
Supplementary

Article: Time-resolved resonance Raman and density functional theory investigation of iodocyclopropanation and addition reactions with alkenes after ultraviolet photolysis of iodoform

TitleTime-resolved resonance Raman and density functional theory investigation of iodocyclopropanation and addition reactions with alkenes after ultraviolet photolysis of iodoform
Authors
Issue Date2002
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2002, v. 67 n. 12, p. 4228-4235 How to Cite?
AbstractA time-resolved resonance Raman spectroscopic investigation is reported for the ultraviolet photolysis of CHI 3 in pure cyclohexene and mixed cyclohexane/cyclohexene solvents. The ICHI-I species is observed in pure cyclohexane solvent. Upon addition of cyclohexene, the ICHI-I species lifetime is reduced and new bands from an I 2:cyclohexene complex are observed. Density functional theory computations show that ICHI-I and CHI 2 species have similar barriers of reaction toward addition to the C=C of ethylene. The addition reaction of ICHI-I with ethylene results in formation of an iodocyclopropane and I 2 molecule while addition of CHI 2 results in initial formation of a diiodopropyl radical intermediate. Ultraviolet photolysis of CHI 3 in the presence of cyclohexene is known to produce a reasonable yield of iodonorcarane product and some addition reaction products. We present a mechanism for the iodocyclopropanation reaction that is consistent with both experimental and theoretical characterization of reaction intermediates formed after ultraviolet photolysis of CHI 3. We briefly discuss the concentration dependence of the time-resolved resonance Raman spectra and photochemistry in relation to the competition between the reaction of the ICHI-I and CHI 2 species with the C=C bond of olefins.
Persistent Identifierhttp://hdl.handle.net/10722/167754
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorLi, YLen_US
dc.contributor.authorChen, DMen_US
dc.contributor.authorWang, Den_US
dc.contributor.authorPhillips, DLen_US
dc.date.accessioned2012-10-08T03:11:03Z-
dc.date.available2012-10-08T03:11:03Z-
dc.date.issued2002en_US
dc.identifier.citationJournal Of Organic Chemistry, 2002, v. 67 n. 12, p. 4228-4235en_US
dc.identifier.issn0022-3263en_US
dc.identifier.urihttp://hdl.handle.net/10722/167754-
dc.description.abstractA time-resolved resonance Raman spectroscopic investigation is reported for the ultraviolet photolysis of CHI 3 in pure cyclohexene and mixed cyclohexane/cyclohexene solvents. The ICHI-I species is observed in pure cyclohexane solvent. Upon addition of cyclohexene, the ICHI-I species lifetime is reduced and new bands from an I 2:cyclohexene complex are observed. Density functional theory computations show that ICHI-I and CHI 2 species have similar barriers of reaction toward addition to the C=C of ethylene. The addition reaction of ICHI-I with ethylene results in formation of an iodocyclopropane and I 2 molecule while addition of CHI 2 results in initial formation of a diiodopropyl radical intermediate. Ultraviolet photolysis of CHI 3 in the presence of cyclohexene is known to produce a reasonable yield of iodonorcarane product and some addition reaction products. We present a mechanism for the iodocyclopropanation reaction that is consistent with both experimental and theoretical characterization of reaction intermediates formed after ultraviolet photolysis of CHI 3. We briefly discuss the concentration dependence of the time-resolved resonance Raman spectra and photochemistry in relation to the competition between the reaction of the ICHI-I and CHI 2 species with the C=C bond of olefins.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jocen_US
dc.relation.ispartofJournal of Organic Chemistryen_US
dc.titleTime-resolved resonance Raman and density functional theory investigation of iodocyclopropanation and addition reactions with alkenes after ultraviolet photolysis of iodoformen_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/jo011163oen_US
dc.identifier.pmid12054958-
dc.identifier.scopuseid_2-s2.0-0037076943en_US
dc.identifier.hkuros73893-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0037076943&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume67en_US
dc.identifier.issue12en_US
dc.identifier.spage4228en_US
dc.identifier.epage4235en_US
dc.identifier.isiWOS:000176173700030-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridLi, YL=27168456500en_US
dc.identifier.scopusauthoridChen, DM=7405450267en_US
dc.identifier.scopusauthoridWang, D=39462302500en_US
dc.identifier.scopusauthoridPhillips, DL=7404519365en_US

Export via OAI-PMH Interface in XML Formats


OR


Export to Other Non-XML Formats