REACTIONS OF ORGANOTIN COMPOUNDS: VI. THE REACTIONS OF TIN HYDRIDES WITH PERFLUOROVINYL TIN COMPOUNDS
- 15 January 1966
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 44 (2) , 179-189
- https://doi.org/10.1139/v66-029
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.Keywords
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