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Issue 24, 2002
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Fluorination of α-phenylsulfanyl esters using difluoroiodotoluene

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Abstract

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.

Graphical abstract: Fluorination of α-phenylsulfanyl esters using difluoroiodotoluene

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Publication details

The article was received on 18 Sep 2002, accepted on 06 Nov 2002 and first published on 22 Nov 2002


Article type: Paper
DOI: 10.1039/B209079A
Citation: J. Chem. Soc., Perkin Trans. 1, 2002,0, 2809-2815
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    Fluorination of α-phenylsulfanyl esters using difluoroiodotoluene

    W. B. Motherwell, M. F. Greaney and D. A. Tocher, J. Chem. Soc., Perkin Trans. 1, 2002, 0, 2809
    DOI: 10.1039/B209079A

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