Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles

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dc.contributor.authorKissane, Marie
dc.contributor.authorMurphy, Maureen
dc.contributor.authorO'Brien, Elisabeth
dc.contributor.authorChopra, Jay
dc.contributor.authorMurphy, Linda.
dc.contributor.authorCollins, Stuart G.
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.funderMerck, United Statesen
dc.contributor.funderUniversity College Corken
dc.date.accessioned2012-06-07T11:10:58Z
dc.date.available2012-06-07T11:10:58Z
dc.date.copyright2011
dc.date.issued2011-04-07
dc.description.abstractSynthetically versatile conjugate addition of a range of carbon, nitrogen, oxygen, sulfur and selenium nucleophiles to the highly functionalised 2-thio-3-chloroacrylamides is described. The stereochemical and synthetic features of this transformation are discussed in detail. In most instances, the nucleophile replaces the chloro substituent with retention of stereochemistry. With the oxygen nucleophiles, a second addition can occur leading to acetals, while with the nitrogen nucleophiles, E-Z isomerism occurs in the resulting enamine derivatives. The ratio of the E/Z isomers can be rationalised on the basis of the substituent and the level of oxidation.en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationKISSANE, M., MURPHY, M., O'BRIEN, E., CHOPRA, J., MURPHY, L., COLLINS, S. G., LAWRENCE, S. E. & MAGUIRE, A. R., 2011. Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles. Organic & Biomolecular Chemistry, 9, 2452-2472. doi: 10.1039/C0OB00805Ben
dc.identifier.doi10.1039/C0OB00805B
dc.identifier.endpage2472en
dc.identifier.issn1477-0520
dc.identifier.issued7en
dc.identifier.journaltitleOrganic and Biomolecular Chemistryen
dc.identifier.startpage2452en
dc.identifier.urihttps://hdl.handle.net/10468/602
dc.identifier.volume9en
dc.language.isoenen
dc.publisherRSC Publishingen
dc.relation.urihttp://pubs.rsc.org/en/content/articlelanding/2011/ob/c0ob00805b
dc.rights©2010, The Authors. Exclusive licence to publish RSC Publishing.en
dc.subject2-thio-3-chloroacrylamidesen
dc.subjectAcetalsen
dc.subjectE-Z Isomerismen
dc.subjectSelenium nucleophilesen
dc.subjectSulfur nucleophilesen
dc.subjectOxygen nucleophilesen
dc.subjectNitrogen nucleophilesen
dc.subjectCarbon based nucleophilesen
dc.subject.lcshNucleophilic reactionsen
dc.subject.lcshOrganic compounds--Synthesisen
dc.subject.lcshOrganic reaction mechanismsen
dc.titleAddition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophilesen
dc.typeArticle (peer-reviewed)en
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