Fluorination of α-phenylsulfanyl esters using difluoroiodotoluene

William B. Motherwell, Michael F. Greaney, Derek A. Tocher

    Research output: Contribution to journalArticlepeer-review


    Treatment of α-phenylsulfanyl esters 11-14 with one equivalent of difluoroiodotoluene 3a produced the α-fluoro sulfides 17-20 in good overall yield through a Fluoro-Pummerer reaction. A second equivalent of reagent produced α,α-difluoro sulfides and a third led to α,α-difluoro sulfoxides. An identical pattern of reactivity was observed with the α-phenylsulfanyl lactone 26. This sequential fluorination-oxidation behaviour was exploited in the one-pot synthesis of 3-fluoro-2(5H)-furanone 33 starting from α-phenylsulfanylbutyrolactone 32.
    Original languageEnglish
    Pages (from-to)2809-2815
    Number of pages6
    JournalJournal of the Chemical Society. Perkin Transactions 1
    Issue number24
    Publication statusPublished - 21 Dec 2002


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