Synthesis of substituted aryltrimethylstannanes by the reaction of trimethylstannylsodium with aryl bromides

The preparation of substituted aryltrimethylstannanes by the reaction of aryl bromides with trimethylstannylsodium in tetraglyme has been studied. Among the substituents present on the aromatic rings were bromine, chlorine, amino, formyl, acetyl and methoxycarbonyl. Factors affecting the success of these and other preparations are discussed in terms of a previously proposed mechanism involving the formation of arylsodium and bromotrimethylstannane as intermediates. These can react with each other in the solvent cage in which they are formed, or after diffusion into the bulk of the solvent. Side reactions can occur by reaction of the arylsodium with functional substituents.