Bis(acylsilanes) and trifluoromethyltrimethylsilane: a useful system for the synthesis of cyclic 2,2-difluoro-3-trialkylsilyl-1,3-ketols and cyclic 2-fluoro-1,3-diketones(1).
We report a one-pot reaction of bis(acylsilanes) with trifluoromethyltrimethylsilane (TFMTMS) leading to a new family of 2,2-difluoro-3-trialkylsilylketols 4. These compounds were submitted to a facile and effective defluorosilylation. The overall process constitutes a new synthesis of cyclic six- and seven-membered 2-fluoro-1,3-diketones 8, with regiospecific introduction of fluorine. The keto-enol equilibrium of cyclic 1,3-diketones and the mechanism of the defluorosilylation reaction were also studied.
Saleur
D
D
Laboratoire Réactions Sélectives et Applications, Associé au CNRS (UMR 6519), Faculté des Sciences, BP 1039, 51687 Reims Cedex 2, France.
Bouillon
J P
JP
Portella
C
C