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 journalArticlepeer-review

63 Citations (Scopus)


(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
Issue number27
Early online date16 Jun 2008
Publication statusPublished - 23 Jun 2008
Externally publishedYes


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