Novel Introduction of a Tetrafluoroethylene (-CF₂CF₂-) Unit into Organic Molecules

Abstract

The reductive coupling of 4-bromo-3,3,4,4-tetrafluorobut-1-ene with 2.4 equivalents of various carbonyl compounds proceeded very smoothly in the presence of 2.4 equivalents of MeLi/LiBr-free at -78 ˚C for two hours, giving the corresponding adducts in high to excellent yields. On the other hand, triethyl(1,1,2,2-tetrafluorobut-3-enyl)silane, which could be prepared by treatment of 4-bromo-3,3,4,4-tetrafluorobut-1-ene and chlorotriethylsilane with magnesium at 0 ˚C for three hours, reacted with some aldehydes in the presence of 1 mol% of tetrabutylammonium fluoride, the desired adducts being obtained in good to high yields.

Key words

tetrafluoroethylene - MeLi/LiBr-free - triethyl(1,1,2,2-tetrafluorobut-3-enyl)silane - reductive coupling

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6

Unpublished results.