Decoupling deprotonation from metalation: Thia-fries rearrangement

Alan M. Dyke, Duncan M. Gill, Jeremy N. Harvey, Alison J. Hester, Guy C. Lloyd-Jones, M. Paz Muñoz, Ian R. Shepperson

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish
Pages (from-to)5067-5070
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number27
Early online date16 Jun 2008
DOIs
Publication statusPublished - 23 Jun 2008
Externally publishedYes

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    Dyke, A. M., Gill, D. M., Harvey, J. N., Hester, A. J., Lloyd-Jones, G. C., Muñoz, M. P., & Shepperson, I. R. (2008). Decoupling deprotonation from metalation: Thia-fries rearrangement. Angewandte Chemie - International Edition, 47(27), 5067-5070. https://doi.org/10.1002/anie.200800750