The direct synthesis of triorganotin compounds: Process and reaction mechanism

The reaction of tin metal with alkyl halides in the presence of a stoichiometric amount of halide ion rapidly produces very high yields of triorganotin halides. An overview of these reaction conditions and those required for the catalytic preparation of diorganotin dihalides shows that these preparations follow the normal reactivity of the alkyl halides towards nucleophiles. Both processes are satisfactorily explained by a mechanism involving tin halogenoanions as nucleophiles. A similar mechanism also explains the formation of organomagnesium and organozinc halides.