Synthetic and mechanistic aspects of sulfonyl migrations

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Date
2020-02-03
Authors
Flynn, Aaran J.
Ford, Alan
Maguire, Anita R.
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Royal Society of Chemistry
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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.
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Keywords
Carbon , Electron spin resonance spectroscopy , Nitrogen , Oxygen , Paramagnetic resonance , Density functional theory
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
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© The Royal Society of Chemistry 2020