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

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dc.contributor.author Kissane, Marie
dc.contributor.author Murphy, Maureen
dc.contributor.author O'Brien, Elisabeth
dc.contributor.author Chopra, Jay
dc.contributor.author Murphy, Linda.
dc.contributor.author Collins, Stuart G.
dc.contributor.author Lawrence, Simon E.
dc.contributor.author Maguire, Anita R.
dc.date.accessioned 2012-06-07T11:10:58Z
dc.date.available 2012-06-07T11:10:58Z
dc.date.copyright 2011
dc.date.issued 2011-04-07
dc.identifier.citation KISSANE, 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/C0OB00805B en
dc.identifier.volume 9 en
dc.identifier.issued 7 en
dc.identifier.startpage 2452 en
dc.identifier.endpage 2472 en
dc.identifier.issn 1477-0520
dc.identifier.uri http://hdl.handle.net/10468/602
dc.identifier.doi 10.1039/C0OB00805B
dc.description.abstract Synthetically 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.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher RSC Publishing en
dc.relation.uri http://pubs.rsc.org/en/content/articlelanding/2011/ob/c0ob00805b
dc.rights ©2010, The Authors. Exclusive licence to publish RSC Publishing. en
dc.subject 2-thio-3-chloroacrylamides en
dc.subject Acetals en
dc.subject E-Z Isomerism en
dc.subject Selenium nucleophiles en
dc.subject Sulfur nucleophiles en
dc.subject Oxygen nucleophiles en
dc.subject Nitrogen nucleophiles en
dc.subject Carbon based nucleophiles en
dc.subject.lcsh Nucleophilic reactions en
dc.subject.lcsh Organic compounds--Synthesis en
dc.subject.lcsh Organic reaction mechanisms en
dc.title Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles en
dc.type Article (peer-reviewed) en
dc.internal.authorurl http://publish.ucc.ie/researchprofiles/V001/amaguire en
dc.internal.authorcontactother Department of Chemistry and School of Pharmacy, Analytical and Biological ChemistryResearch Facility, University College Cork, Ireland. Tel. no.: +353 (0)21 4901694. E-mail: a.maguire@ucc.ie en
dc.internal.availability Full text available en
dc.description.version Accepted Version en
dc.internal.rssid 82036040
dc.contributor.funder Irish Research Council for Science Engineering and Technology en
dc.contributor.funder Forbairt en
dc.contributor.funder Merck, United States en
dc.contributor.funder University College Cork en
dc.description.status Peer reviewed en
dc.identifier.journaltitle Organic and Biomolecular Chemistry en
dc.internal.copyrightchecked Checked publisher's website, via Sherpa Romeo. Added text as required by RSC - (b) The Author(s) may deposit the accepted version of the submitted Paper in their institutional repository(ies). There shall be an embargo of making the above deposited material available to the public of 12 months from the date of acceptance. There shall be a link from this Paper to the final (PDF) version of the Paper on the RSC’s website once this final version is available. Date of Acceptance = 17th December 2010 = Embargo now expired en
dc.internal.IRISemailaddress a.maguire@ucc.ie en
dc.internal.IRISemailaddress simon.lawrence@ucc.ie en


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