5-Azidotetrazoles

A photolytic study with a 5-azidotetrazole derivative also led to the formation of a tetrazolo[l,5-/z]quinazoline compound, although the yield was fairly low. Araki et al. published findings that irradiation of 110 in aqueous medium resulted in formation of the mesoionic enolate 112 in 8% yield <2000JHC1129> (Scheme 20). The authors concluded that the formation of the tricyclic structure can be rationalized by an intramolecular insertion of the triplet nitrene formed from 110 to a C-H bond of an ortho-methyl group to give at first intermediate 111, which was converted under the applied reaction conditions to produce 112. 

The reaction of aminoguanidine with sodium nitrite under neutral conditions yields tetra-zolylguanyltetrazene hydrate (85), a primary explosive commonly known as tetrazene. Tetrazene (85) is only formed in the absence of free mineral acid and so a common method for its preparation treats the bicarbonate salt of aminoguanidine (84) with one equivalent of acetic acid followed by addition of aqueous sodium nitrite. " Tetrazene (85) is decomposed by aqueous alkali to form triazonitrosoaminoguanidine (86) which is isolated as the cuprate salt (87) on addition of copper acetate to the reaction mixture. Acidification of the copper salt (87) with mineral acid leads to the formation of 5-azidotetrazole (88) (CHN7 = 88 % N).55 56... 

Hydroxy tetrazole l-Hydroxy-5-azidotetrazole 5-Hydroxy tetrazole Hydroxy tetrazolylmethanol Hydroxytetrazolylmethanol Nitrate... 

The salts of 5-Nitrotetrazole could also be ranked according to their sensitiveness. The salts of Ag, Hg, and Pb gave more sensitive compns and greater initiating power than the alkali metal salts. The same salts of 5-Chloro-tetrazole were too sensitive and corrosive, and those of 5-Azidotetrazole were too hazardous (Ref 9b)... 

Silver-bis-5 -azidotetrazole Too sensitive to handle. When dry will explode if touched with rubber spatula ... 

Azidotetrazole Can be handled when dry but very destructive when explodes ... 

Amino-2-ethyl-2//-tetrazole, 1264 5-Aminotetrazole, 0460 5-Azidotetrazole, 0387 Barium 5,5 -azotetrazolide, 0574 l,6-Bis(5-tetrazolyl)hexaaza-l,5-diene, 0823... 

Caution We have observed that on treating 2-methyl-5-nitrotetrazole with NaN3 in HzO solution a product is formed that is prone to spontaneous explosive decomposition. Apparently, under similar conditions, the nitro group is replaced by the azido group giving the corresponding 5-azidotetrazole derivative. 

Azidotetrazole and Acetone. Mixture explodes if traces of acetic acid are present.6... 

Azido-l-Phenyl-5-Azidobenzene (1-Phenyl-5-Azidotetrazole). See under Phenyltetrazole... 

Potentially explosive reaction with 5-azidotetrazole, bromine pentafluoride, chromium trioxide, hydrogen peroxide, potassium permanganate, sodium peroxide, and phosphorus trichloride. Potentially violent reactions with acetaldehyde and acetic anhydride. Ignites on contact with... 

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