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Synthetic and mechanistic aspects of sulfonyl migrations
- Source :
- Organic & Biomolecular Chemistry. 18:2549-2610
- Publication Year :
- 2020
- Publisher :
- Royal Society of Chemistry (RSC), 2020.
-
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.
- Subjects :
- Electron paramagnetic resonance spectroscopy
Sulfonyl
chemistry.chemical_classification
Nitrogen
010405 organic chemistry
Chemistry
Organic Chemistry
Reaction type
010402 general chemistry
01 natural sciences
Biochemistry
Carbon
0104 chemical sciences
Oxygen
Computational chemistry
Electron spin resonance spectroscopy
Density functional theory
Physical and Theoretical Chemistry
Paramagnetic resonance
Subjects
Details
- ISSN :
- 14770539 and 14770520
- Volume :
- 18
- Database :
- OpenAIRE
- Journal :
- Organic & Biomolecular Chemistry
- Accession number :
- edsair.doi.dedup.....bf0d4872b0625d64c39a2e4f18704707