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.

Bibliographical metadata

Original languageEnglish
Pages (from-to)2809-2815
Number of pages6
JournalJournal of the Chemical Society. Perkin Transactions 1
Issue number24
DOIs
StatePublished - 21 Dec 2002