Investigation of the reaction of α-Thioamides, α-esters and α–nitriles with N-halosuccinimides

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dc.contributor.authorKissane, Marie
dc.contributor.authorMurphy, Maureen
dc.contributor.authorLynch, Denis
dc.contributor.authorFord, Alan
dc.contributor.authorMaguire, Anita R.
dc.contributor.funderIrish Research Council for Science Engineering and Technologyen
dc.contributor.funderBioResearch Irelanden
dc.contributor.funderForbairten
dc.contributor.funderUniversity College Corken
dc.date.accessioned2012-05-14T15:48:20Z
dc.date.available2012-05-14T15:48:20Z
dc.date.copyright2008-08-04
dc.date.issued2008-08-04
dc.description.abstractInvestigation of the reaction of α-thioamides, α-esters and α-nitriles with NBS and NCS is described. The scope of this stereoselective oxidative transformation to the β- haloacrylamides, β-acrylates and β–acrylonitriles has been determined. A mechanistic rationale to explain the observed differences in reactivity between the amide, ester and nitrile series is proposed.en
dc.description.statusPeer revieweden
dc.description.versionSubmitted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationKISSANE, M., MURPHY, M., LYNCH, D., FORD, A. & MAGUIRE, A. R. 2008. Investigation of the reaction of α-thioamides, α-esters and α-nitriles with N-halosuccinimides. Tetrahedron, 64, 7639-7649. doi: 10.1016/j.tet.2008.05.026en
dc.identifier.doi10.1016/j.tet.2008.05.026
dc.identifier.endpage7649en
dc.identifier.issn0040-4020
dc.identifier.issued32en
dc.identifier.journaltitleTetrahedronen
dc.identifier.startpage7639en
dc.identifier.urihttps://hdl.handle.net/10468/586
dc.identifier.volume64en
dc.language.isoenen
dc.publisherElsevieren
dc.rightsCopyright © 2008 Elsevier Ltd. All rights reserved. NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron, [VOL 64, ISSUE 32, (04/08/2008)] DOI 10.1016/j.tet.2008.05.026en
dc.subjectalpha-thioamidesen
dc.subjectalpha-estersen
dc.subjectalpha-nitrilesen
dc.subjectN-Bromosuccinimide(NBS)en
dc.subjectN-Chlorosuccinimide (NCS)en
dc.subjectbeta-haloacrylamidesen
dc.subjectbeta-acrylatesen
dc.subjectbeta–acrylonitrilesen
dc.titleInvestigation of the reaction of α-Thioamides, α-esters and α–nitriles with N-halosuccinimidesen
dc.typeArticle (peer-reviewed)en
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