Synthetic and mechanistic aspects of sulfonyl migrations

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dc.contributor.author Flynn, Aaran J.
dc.contributor.author Ford, Alan
dc.contributor.author Maguire, Anita R.
dc.date.accessioned 2020-06-12T10:19:02Z
dc.date.available 2020-06-12T10:19:02Z
dc.date.issued 2020-02-03
dc.identifier.citation Flynn, A. J., Ford, A. and Maguire, A. (2020) 'Synthetic and mechanistic aspects of sulfonyl migrations', Organic & Biomolecular Chemistry, 18(14), pp. 2549-2610. doi: 10.1039/C9OB02587A en
dc.identifier.volume 18 en
dc.identifier.issued 14 en
dc.identifier.startpage 2549 en
dc.identifier.endpage 2610 en
dc.identifier.issn 1477-0520
dc.identifier.uri http://hdl.handle.net/10468/10142
dc.identifier.doi 10.1039/C9OB02587A en
dc.description.abstract Over the past 20 years reports of sulfonyl migrations have appeared, frequently described as ‘unusual’ and ‘unexpected’. This comprehensive review compiles, for the first time, sulfonyl migrations reported over the last 20 years including formal 1,2-, 1,3-, 1,4-, 1,5-, 1,6- and 1,7-sulfonyl shifts, occurring through either radical or polar processes, either inter- or intramolecularly. Discussion of the sulfonyl migrations is structured according to reaction type, i.e. nitrogen–carbon, nitrogen–oxygen, nitrogen–nitrogen, oxygen–carbon (including anionic and non-anionic thia-Fries rearrangements), oxygen–oxygen and carbon–carbon migrations. Discussion of the underlying mechanisms for the migrations is included, with particular attention afforded to the principal techniques utilised for their elucidation, namely isotopic-labelling, crossover experiments, density functional theory calculations and electron paramagnetic resonance spectroscopy amongst others. en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher Royal Society of Chemistry en
dc.relation.uri https://pubs.rsc.org/en/content/articlelanding/2020/OB/C9OB02587A
dc.rights © The Royal Society of Chemistry 2020 en
dc.subject Carbon en
dc.subject Electron spin resonance spectroscopy en
dc.subject Nitrogen en
dc.subject Oxygen en
dc.subject Paramagnetic resonance en
dc.subject Density functional theory en
dc.title Synthetic and mechanistic aspects of sulfonyl migrations en
dc.type Article (preprint) en
dc.internal.authorcontactother Anita Maguire, Chemistry, University College Cork, Cork, Ireland. +353-21-490-3000 Email: a.maguire@ucc.ie en
dc.internal.availability Full text available en
dc.check.info Access to this article is restricted until 12 months after publication by request of the publisher. en
dc.check.date 2021-02-03
dc.description.version Accepted Version en
dc.internal.rssid 510842719
dc.contributor.funder Science Foundation Ireland en
dc.contributor.funder European Regional Development Fund en
dc.description.status Peer reviewed en
dc.identifier.journaltitle Organic and Biomolecular Chemistry en
dc.internal.IRISemailaddress a.maguire@ucc.ie en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/ en
dc.identifier.eissn 1477-0539


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