dc.contributor.author |
Flynn, Aaran J. |
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dc.contributor.author |
Ford, Alan |
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dc.contributor.author |
Maguire, Anita R. |
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dc.date.accessioned |
2020-06-12T10:19:02Z |
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dc.date.available |
2020-06-12T10:19:02Z |
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dc.date.issued |
2020-02-03 |
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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 |
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dc.identifier.startpage |
2549 |
en |
dc.identifier.endpage |
2610 |
en |
dc.identifier.issn |
1477-0520 |
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dc.identifier.uri |
http://hdl.handle.net/10468/10142 |
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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 |
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dc.rights |
© The Royal Society of Chemistry 2020 |
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dc.subject |
Carbon |
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dc.subject |
Electron spin resonance spectroscopy |
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dc.subject |
Nitrogen |
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dc.subject |
Oxygen |
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dc.subject |
Paramagnetic resonance |
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dc.subject |
Density functional theory |
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dc.title |
Synthetic and mechanistic aspects of sulfonyl migrations |
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dc.type |
Article (preprint) |
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dc.internal.authorcontactother |
Anita Maguire, Chemistry, University College Cork, Cork, Ireland. +353-21-490-3000 Email: a.maguire@ucc.ie |
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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 |
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dc.description.version |
Accepted Version |
en |
dc.internal.rssid |
510842719 |
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dc.contributor.funder |
Science Foundation Ireland
|
en |
dc.contributor.funder |
European Regional Development Fund
|
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dc.description.status |
Peer reviewed |
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dc.identifier.journaltitle |
Organic and Biomolecular Chemistry |
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dc.internal.IRISemailaddress |
a.maguire@ucc.ie |
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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 |
|