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.author Kissane, Marie
dc.contributor.author Lynch, Denis
dc.contributor.author Chopra, Jay
dc.contributor.author Lawrence, Simon E.
dc.contributor.author Maguire, Anita R.
dc.date.accessioned 2012-05-23T11:16:21Z
dc.date.available 2012-05-23T11:16:21Z
dc.date.copyright 2010
dc.date.issued 2010-10-07
dc.identifier.citation KISSANE, 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/C0OB00368A en
dc.identifier.volume 8 en
dc.identifier.issued 24 en
dc.identifier.startpage 5602 en
dc.identifier.endpage 5613 en
dc.identifier.issn 1477-0520
dc.identifier.issn 1477-0539
dc.identifier.uri http://hdl.handle.net/10468/594
dc.identifier.doi 10.1039/C0OB00368A
dc.description.abstract The 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.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/2010/ob/c0ob00368a
dc.rights ©2010, The Authors. Exclusive licence to publish RSC Publishing. en
dc.subject Diels-Alder en
dc.subject Cycloadditions en
dc.subject Cyclopentadiene en
dc.subject 2,3-dimethyl-1,3-butadiene en
dc.subject 2-thio-3-chloroacrylamides en
dc.subject Cycloadducts en
dc.subject Stereoselectivity en
dc.subject.lcsh Organic compounds--Synthesis en
dc.subject.lcsh Oxidation en
dc.title The influence of reaction conditions on the Diels-Alder cycloadditions of 2-thio-3-chloroacrylamides; investigation of thermal, catalytic and microwave conditions 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 Chemistry Research Facility, University College Cork, Ireland. T.:+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 67960166
dc.contributor.funder Irish Research Council for Science Engineering and Technology en
dc.contributor.funder Forbairt 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 policy on: /www.rsc.org/AboutUs/Copyright/Authordeposition.asp http:/Allowed Deposition by the author(s) When the author accepts the exclusive Licence to Publish for a journal article, he/she retains certain rights concerning the deposition of the whole article. He/she may: •Deposit the accepted version of the submitted article 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 article to the PDF of the final published article on the RSC's website once this final version is available. en
dc.internal.IRISemailaddress a.maguire@ucc.ie en
dc.internal.IRISemailaddress simon.lawrence@ucc.ie en


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