The Formation of Tin-Nitrogen Bonds. V. The Selective 1-Substitution Reaction of Tetrazoles by the Reaction of 5-Substituted 2-(Tri-n-butylstannyl)tetrazoles with Methyl Iodide, Methyl p-Toluenesulfonate, Dimethyl Sulfate, and Ethyl Bromoacetate

The selective 1-substitution reaction of tetrazole was developed by the treatment of 5-substituted 2-(tri-n-butylstannyl)tetrazoles with methyl iodide, methyl p-toluenesulfonate, dimethyl sulfate, or ethyl bromoacetate at room temperature. This selectivity was introduced by blocking the 2-nitrogen with the tri-n-butyltin group against the 2-substitution. In the case of 5-substituted 2-(trimethylstannyl)tetrazoles, a low selectivity was observed. The possible reaction pathways have been discussed.