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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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    Abstract

    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 12:27
    Last Modified: 19 Sep 2013 16:44
    URI: http://eprints.hud.ac.uk/id/eprint/14876

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