Decoupling Deprotonation from Metalation: Thia-Fries Rearrangement

Decoupling Deprotonation from Metalation: Thia-Fries Rearrangement

Label‐enabled: Studies with 2H‐, 18O‐, and 34S‐labeled aryl triflates show that lithium diisopropylamide‐mediated thia‐Fries rearrangement proceeds through an irreversible ortho deprotonation (see scheme; DIPA=diisopropylamine, LDA=lithium diisopropylamide). In contrast, ortho metalation results exc...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2008-06, Vol.47 (27), p.5067-5070
Hauptverfasser: Dyke, Alan M, Gill, Duncan M, Harvey, Jeremy N, Hester, Alison J, Lloyd-Jones, Guy C, Muñoz, M. Paz, Shepperson, Ian R
Format: Artikel
Sprache:eng
Schlagworte:
basicity
Benzene Derivatives - chemical synthesis
Benzene Derivatives - chemistry
metalation
migration
Molecular Structure
Propylamines - chemistry
Protons
rearrangements
superbases
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Zusammenfassung:Label‐enabled: Studies with 2H‐, 18O‐, and 34S‐labeled aryl triflates show that lithium diisopropylamide‐mediated thia‐Fries rearrangement proceeds through an irreversible ortho deprotonation (see scheme; DIPA=diisopropylamine, LDA=lithium diisopropylamide). In contrast, ortho metalation results exclusively in the generation of a benzyne.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200800750