Tetrazenes, decomposition, nitrogen

In the first stage of the reaction an alkoxyl anion and the nitrohydrazine cation are formed which afterwards react together to give the corresponding alcohol and nitrohydrazine. Nitrohydrazine reacts with excess hydrazine to produce tetrazene, nitrous acid and di-imid. Then the tetrazene decomposes to form ammonia and nitrogen from di-imid on the other hand tetrazene, hydrazine and nitrogen are formed. Hydrazoic acid and ammonia are then formed as decomposition products of tetrazene. 

With the intention of extending the nitrogen chain of tetrazene, tet-razenides 62 and 64 were allowed to react with nitrogen halides as well as their derivatives. The desired objective could not be reached in any case because of decomposition of the expected compounds. Thus, reactions of 62 with nitrosyl chloride (NOX X = Cl) and 64 with isoamyl nitrite (NOX X = 0(/-CsHn)] at low temperature in ether occur according to Eqs. (95) and (96) via 73 and 74 (45), respectively, whereas reactions of 62 with phenyldiazonium chloride (PhN=N Cl ) or tosyl azide (TsN, Ts = P-T0ISO2) at — 78°C develop according to Eqs. (97) and (98), probably via 75 and 76, respectively. 

C to hydrazine and nitrogen gas. Draw a Lewis structure for tetrazene, and calculate for this decomposition. 

The preferred transoid geometry of tetraalkyl-2-tetrazenes is in common with other azo compounds. In this case, however, the cisoid form of the acylic tetrazenes has never been isolated. In fact Roberts and Ingold (5 suggested that the photochemical decomposition of tetrazenes involved the photochemical trans to cis isomerization followed by the thermal loss of nitrogen from the cis-isomer. Some acylated cis-tetrazenes have been reported (54,55), but the chemical behavior of these substances differs substantially from the tetraalkyl analogs. 

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