Triazine triazide

Cyanuric Triazide (called Cyanurtriazid or 2,4.6 -Triazido - 1,3.5 triazin in Ger),... 

Cyanuric Triazide. See in Vol 3, C590-R to C591-L, and under Triazines in this Vol... 

Stepwise generation of mononitrene, dinitrene, and trinitrene by the matrix photolysis of 2,4,6-triazido-l,3,5-triazine 42 (cyanuric triazide) was observed by matrix IR and electron paramagnetic resonance (EPR) spectroscopy (Scheme 5). The generated species were identified by comparison of their matrix IR spectra with DET computational results <2004JA7846>. 

Cyanuric triazide (2,4,6-triazido-l,3,5-triazine TAT sometimes called simply triazide ) was probably first prepared by H. Finger in 1907 by the reaction of 2,4,6-trihydrazino-l,3,5-triazine with sodium nitrite in an acidic environment [6,46,128]. 

Tetra(chIoro)hydrazo-l,3,5-triaziiie (prepared from cyanuric triazide [151]) is the starting material for both compounds. Its reaction with excess of hydrazine hydrate in acetonitrile forms 4,4, 6,6 -tetra(hydrazino)hydrazo-l,3,5-tri-azine which undergoes diazotization to TAHT. TAAT forms by oxidation of TAHT by chlorine in a water/chloroform suspension [147,148,150]. Simplified method of preparation of the key intermediate TAHT was pubhshed by Li et al. [152]. Instead of hydrazinolysis and diazotation they used nucleophilic substitution of 4,4, 6,6 -tetra(chloro)hydrazo-l,3,5-triazine with sodium azide for preparation of TAHT which they in the last step oxidized with A-bromosuccinimide. 

---