Synthetic and mechanistic aspects of sulfonyl migrations

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dc.contributor.authorFlynn, Aaran J.
dc.contributor.authorFord, Alan
dc.contributor.authorMaguire, Anita R.
dc.contributor.funderScience Foundation Irelanden
dc.contributor.funderEuropean Regional Development Funden
dc.date.accessioned2020-06-12T10:19:02Z
dc.date.available2020-06-12T10:19:02Z
dc.date.issued2020-02-03
dc.description.abstractOver 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.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationFlynn, 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/C9OB02587Aen
dc.identifier.doi10.1039/C9OB02587Aen
dc.identifier.eissn1477-0539
dc.identifier.endpage2610en
dc.identifier.issn1477-0520
dc.identifier.issued14en
dc.identifier.journaltitleOrganic and Biomolecular Chemistryen
dc.identifier.startpage2549en
dc.identifier.urihttps://hdl.handle.net/10468/10142
dc.identifier.volume18en
dc.language.isoenen
dc.publisherRoyal Society of Chemistryen
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/en
dc.relation.urihttps://pubs.rsc.org/en/content/articlelanding/2020/OB/C9OB02587A
dc.rights© The Royal Society of Chemistry 2020en
dc.subjectCarbonen
dc.subjectElectron spin resonance spectroscopyen
dc.subjectNitrogenen
dc.subjectOxygenen
dc.subjectParamagnetic resonanceen
dc.subjectDensity functional theoryen
dc.titleSynthetic and mechanistic aspects of sulfonyl migrationsen
dc.typeArticle (preprint)en
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