Preparation of organofunctional bis(stannyl)methanes. Intramolecular coordination in the halo derivatives

Article abstract of DOI:10.1021/om50001a024

The preparation of a series of 3,3-bis(trimethylstannyl)-, 3,3-bis(halodimethylstannyl)-, and 3,3-bis (dihalomethylstannyl)propyl derivatives having carboxyl, hydroxy, acetoxy, and sulfoxy as functional groups is described. Intramolecular coordination in the bromostannyl acetates and sulfoxides was examined. 3,3-Bis(bromodimethylstannyl)propyl acetate showed no evidence of coordination in the solid state or in acetonitrile as shown by IR study; the bis(dibromomethylstannyl) analogue showed coordination of the acetate carbonyl to tin in the solid state but not in acetonitrile. Each of the corresponding sulfoxides showed coordination between oxygen and tin in the soid state and in solution. The coordination is probably by way of bridging between the geminal tin atoms rather than coordination to a single tin; it was shown that the complexes are stable on the ¹H, ¹³C, and ¹¹⁹Sn time scales at normal operating probe temperatures.