Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 14, Pages 2549-2610Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9ob02587a
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Funding
- Synthesis and Solid State Pharmaceutical Centre
- Science Foundation Ireland
- European Regional Development Fund [12/RC/2275]
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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.
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