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Decoupling Deprotonation from Metalation: Thia-Fries Rearrangement

Gill, Duncan M., Dyke, Alan, Harvey, Jeremy, Hester, Alison, Lloyd-Jones, Guy, Paz Munoz, Maria and Sheperson, Ian (2008) Decoupling Deprotonation from Metalation: Thia-Fries Rearrangement. Angewandte Chemie International Edition, 47 (27). pp. 5067-5070. ISSN 14337851

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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.

Item Type: Article
Subjects: Q Science > QD Chemistry
Schools: School of Applied Sciences
Depositing User: Duncan Gill
Date Deposited: 27 Sep 2012 11:27
Last Modified: 19 Sep 2013 15:44


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