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Issue 14, 2020
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Synthetic and mechanistic aspects of sulfonyl migrations

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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.

Graphical abstract: Synthetic and mechanistic aspects of sulfonyl migrations

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Article information

04 Dec 2019
03 Feb 2020
First published
03 Feb 2020

Org. Biomol. Chem., 2020,18, 2549-2610
Article type
Review Article

Synthetic and mechanistic aspects of sulfonyl migrations

A. J. Flynn, A. Ford and A. R. Maguire, Org. Biomol. Chem., 2020, 18, 2549
DOI: 10.1039/C9OB02587A

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