The influence of reaction conditions on the Diels-Alder cycloadditions of 2-thio-3-chloroacrylamides; investigation of thermal, catalytic and microwave conditions

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dc.contributor.authorKissane, Marie
dc.contributor.authorLynch, Denis
dc.contributor.authorChopra, Jay
dc.contributor.authorLawrence, Simon E.
dc.contributor.authorMaguire, Anita R.
dc.contributor.funderIrish Research Council for Science Engineering and Technologyen
dc.contributor.funderForbairten
dc.contributor.funderUniversity College Corken
dc.date.accessioned2012-05-23T11:16:21Z
dc.date.available2012-05-23T11:16:21Z
dc.date.copyright2010
dc.date.issued2010-10-07
dc.description.abstractThe Diels-Alder cycloadditions of cyclopentadiene and 2,3-dimethyl-1,3-butadiene to a range of 2-thio-3-chloroacrylamides under thermal, catalytic and microwave conditions is described. The influence of reaction conditions on the outcome of the cycloadditions, in particular the stereoselectivity and reaction efficiency, is discussed. While the cycloadditions have been attempted at the sulfide, sulfoxide and sulfone levels of oxidation, use of the sulfoxide derivatives is clearly beneficial for stereoselective construction of Diels-Alder cycloadducts.en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationKISSANE, M., LYNCH, D., CHOPRA, J., LAWRENCE, S. E. & MAGUIRE, A. R. 2010. The influence of reaction conditions on the Diels-Alder cycloadditions of 2-thio-3-chloroacrylamides; investigation of thermal, catalytic and microwave conditions. Organic & Biomolecular Chemistry, 8, 5602-5613. doi: 10.1039/C0OB00368Aen
dc.identifier.doi10.1039/C0OB00368A
dc.identifier.endpage5613en
dc.identifier.issn1477-0520
dc.identifier.issn1477-0539
dc.identifier.issued24en
dc.identifier.journaltitleOrganic and Biomolecular Chemistryen
dc.identifier.startpage5602en
dc.identifier.urihttps://hdl.handle.net/10468/594
dc.identifier.volume8en
dc.language.isoenen
dc.publisherRSC Publishingen
dc.relation.urihttp://pubs.rsc.org/en/content/articlelanding/2010/ob/c0ob00368a
dc.rights©2010, The Authors. Exclusive licence to publish RSC Publishing.en
dc.subjectDiels-Alderen
dc.subjectCycloadditionsen
dc.subjectCyclopentadieneen
dc.subject2,3-dimethyl-1,3-butadieneen
dc.subject2-thio-3-chloroacrylamidesen
dc.subjectCycloadductsen
dc.subjectStereoselectivityen
dc.subject.lcshOrganic compounds--Synthesisen
dc.subject.lcshOxidationen
dc.titleThe influence of reaction conditions on the Diels-Alder cycloadditions of 2-thio-3-chloroacrylamides; investigation of thermal, catalytic and microwave conditionsen
dc.typeArticle (peer-reviewed)en
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