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Fluorination of alpha-phenylsulfanyl esters using difluoroiodotoluene

Motherwell, WB; Greaney, MF; Tocher, DA; (2002) Fluorination of alpha-phenylsulfanyl esters using difluoroiodotoluene. J CHEM SOC PERK T 1 (24) 2809 - 2815. 10.1039/b209079a.

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Abstract

Treatment of alpha-phenylsulfanyl esters 11-14 with one equivalent of difluoroiodotoluene 3a produced the alpha-fluoro sulfides 17-20 in good overall yield through a Fluoro-Pummerer reaction. A second equivalent of reagent produced alpha,alpha-difluoro sulfides and a third led to alpha,alpha-difluoro sulfoxides. An identical pattern of reactivity was observed with the alpha-phenylsulfanyl lactone 26. This sequential fluorination-oxidation behaviour was exploited in the one-pot synthesis of 3-fluoro-2(5H)-furanone 33 starting from alpha-phenylsulfanylbutyrolactone 32.

Type: Article
Title: Fluorination of alpha-phenylsulfanyl esters using difluoroiodotoluene
DOI: 10.1039/b209079a
Keywords: IODOTOLUENE DIFLUORIDE, OXIDATIVE-FLUORINATION, IODOARENE DIFLUORIDES, FLUORO THIOETHERS, XENON DIFLUORIDE, FACILE SYNTHESIS, SULFIDES, ANALOGS, ALKENES, REARRANGEMENT
UCL classification: UCL > School of BEAMS > Faculty of Maths and Physical Sciences
UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry
URI: http://discovery.ucl.ac.uk/id/eprint/74411
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