Reactions of 1-Substituted 5-Tetrazolyllithium Compounds; Preparation of 5-Substituted 1-Methyltetrazoles

Abstract

1-Methyl-5-tetrazolyllithium undergoes fragmentation to nitrogen and lithium methylcyanamide at temperatures exceeding −50°. Below −60° it is however fairly stable and a useful reagent for the preparation of various 5-substituted 1-methyltetrazoles. It reacts readily with halogens, cyanogen bromide, sulfur, aldehydes, ketones, and acid chlorides but not appreciably with benzyl bromide and benzonitrile. With methyl benzoate it forms a labile addition compound which can be hydrolyzed to 5-benzoyl-1-methyl-tetrazole.1-Phenyl-5-tetrazolyllithium rapidly decomposes to lithium phenylcyanamide at temperatures as low as −65° to −70°.