Comparative Study of Tris(trifluoromethyl)phosphine Oxide, Tris(nonafluorobutyl)phosphine Oxide, and Fluorobis(nonafluorobutyl)phosphine Oxide with Ammonia and Amines

摘要

Although Burg earlier demonstrated that tris (trifluoromethyl)phosphine oxide gave (dimethylamino)bis(trifluoromethyl)phosphine oxide with dimethylamine,1 little has been reported since that time on the interactions of bis- or tris(perfluoroalkyl)phosphine oxides with ammonia or amines. This may have been in part to the lack of easy availability of the appropriate precursors. We were particularly interested in the hydrolytic stability of these highly fluorinated materials that contain phosphorus-nitrogen-hydrogen bonds. Unfortunately no evidence for stability in aqueous solutions was found. However, we did find quite striking differences in behavior between the title compounds and ammonia or organic bases in some cases. As a result of our study, we have synthesized a variety of tris-, bis, and mono(perfluoroalkyl)phosphorus(V) derivatives. Iodobis(trifluoromethyl)phosphine, (CF3)2PI, and tris(trifluoromethyl)phosphine were prepared by the Emeleus method of causing white phosphorus to react with CF3I. Keywords: Organic amines; Dichloro(pentafluoroethyl)phosphine; Reprints. (aw)