Preparation of 5-Dinitromethyltetrazole from Salts of Dinitroacetonitrile

An attempt was made to prepare the previously unknown dinitromethyltetrazole by the reaction of dinitroacetonitrile and sodium azide in water but with negative results probably due to generation of the sodium salt of dinitroacetonitrile and the highly associated hydrazoic acid. This led to an examination of the reactions of salts of dinitroacetonitrile with sodium or ammonium dinitroacetonitrile (but not the potassium salt) with sodium azide and ammonium chloride (mole ratio 1.00: 1.02: 1.02, respectively) in refluxing water but not in dimethylformamide. This appears to be the first example of the use of an organonitrile salt to form a tetrazole and is the first example of a 5-nitroalkyltetrazole.