ORGANOTIN CHEMISTRY .16. REACTIONS OF STANNANE WITH ORGANIC FUNCTIONAL-GROUPS

The reactions of stannane with a variety of organic substrates have been studied. Benzaldehyde, acetone, nitrobenzene, and 2-nitropropane are reduced to benzyl alcohol, isopropyl alcohol, aniline, and isopropylamine, respectively. With boron trifluoride etherate and benzyl chloride, stannane undergoes halogen-hydrogen exchange, while with isopropylamine and acetic acid, it is decomposed catalytically into its elements. Tetrakis(2-cyanoethyl)tin is formed by the addition of stannane to acrylonitrile. Stannane did not react with the following: (a) ethyl acetate, (b) methyl acrylate, (c) aniline, (d) triethylamine, (e) dimethylacetamide, and (f) N-ethylacetamide. The results obtained with stannane are for the most part analogous to those reported for the corresponding organotin hydrides.