Reactions of Alicyclic Perfluoroimines with Trimethyl(trifluoromethyl)silane

Abstract

Trifluoromethylation of the alicyclic perfluoroimines, perfluoro(5,6-dihydro-2H-1,4-oxazine) (1) and perfluoro(3,4-dihydro-2H-pyrrole) (2), was achieved by using trimethyl(trifluoromethyl)silane (3). Successive trifluoromethylations occurred even when an equimolar amount of 3 was used in both cases so that mono-, di-, and tri-substituted products were formed. In addition to this successive trifluoromethylation, the dimer formation was accompanied in the case of 2, giving three dimers with or without trifluoromethyl substitutents. The reaction mechanism and the solvent effect on the orientation of the trifluoromethylation and the product distribution were discussed. The influence of the substitution of the fluorine bonded to imidoyl carbon of 1 and 2 for a 2,2,2-trifluoroethoxy group on the trifluoromethylation reaction was also investigated.