Perfluoroalkyltin compounds

Fluoroalkyl groups are easily removed from tin by aqueous base (46, 73-75). Fluoroform is liberated quantitatively when trimethylperfluoromethyltin is treated with aqueous alkali in the cold (77). Even hot water will produce monohydro-perfluoroalkanes from the perfluoroalkyltin compounds. A similar easy hydrolysis to afford monohydro-perfluoroalkanes occurs with perfluoroalkyllead, -germanium, and -antimony compounds. Moreover, fluoroalkyl derivatives of transition metals are also very easily decomposed by aqueous alkali, but fluoroalkanes are not a principal decomposition product (Section VI). 

Perfluoroalkyltin halides can be prepared via oxidative addition of perfluo-roalkyl iodides to tin(II) halides in dimethylformamide (DMF) [12] The per-fluoroalkyltin(IV) dihalide could not be isolated, but in DMF solution, the tin(lV) compound did react with aldehydes and ketones in the presence of pyndine [12] (equation 8) Typical perfluoroalkylcarbinols prepared by this method are shown in Table 1 [12]... 

Table 1. Perfluoroalkylation of Carbonyl Compounds by Perfluoroalkyltin(rV) Halides [/2]...

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