Motherwell, WB and Greaney, MF and Tocher, DA (2002) Fluorination of alpha-phenylsulfanyl esters using difluoroiodotoluene. J CHEM SOC PERK T 1 (24) 2809 - 2815. 10.1039/b209079a.
Full text not available from this repository.
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 > Chemistry |
Archive Staff Only: edit this record