REACTIONS OF ORGANOTIN COMPOUNDS: VI. THE REACTIONS OF TIN HYDRIDES WITH PERFLUOROVINYL TIN COMPOUNDS

Abstract

The reactions of methyltin hydrides with methylperfluorovinyltin compounds have been examined under heat or ultraviolet irradiation. In no case is there evidence of addition to the C=C bond. Instead, extensive reduction of the vinyl group occurs to give cis-1,2-difluorovinyltin derivatives as the principal products, with smaller amounts of the trans-1,2-difluorovinyltin isomers, 2,2′-difluorovinyltin compounds, and products containing one or more —C2H2F groups. Trimethyl- or dimethyl-tin fluoride is formed quantitatively from the corresponding hydride. In the reaction of dimethyl bis(perfluorovinyl)tin with dimethyltin dihydride, vinyl-hydrogen exchange occurs at 60° in the dark to give dimethylperfluorovinyltin hydride, while under ultraviolet irradiation partially fluorinated vinyltin compounds are formed. On the other hand, no reaction takes place between dimethyl bis(perfluorovinyl)tin and 2 moles of trimethyltin hydride in the dark at 50°, but under ultraviolet irradiation at 25°, partial vinyl-hydrogen exchange occurs, accompanied by reduction, to yield both trimethyl and dimethyl partially fluorinated vinyltin compounds. The infrared and proton magnetic resonance spectra of the products are discussed.