Hexamethylenetetramine thermal decomposition

Photolysis in the vacuum ultraviolet (1800-2400 A) resulted in the formation of nitrogen, ammonia and hexamethylenetetramine, in yields similar to the thermal decomposition. Hexamethyenetetramine was also a major product in photol-yses above 2400 A and it seems probable that both the thermal and photochemical decompositions proceed by the same mechanism. The solution photolysis of methyl azide has recently been examined and the general kinetic features are similar to the vapor-phase photolysis and thermolysis. Thus increases with CH3N3 concentration to a maximum of 2, and hexamethylenetetramine and N2 were the major products. It is believed that in solution CH3N does not isomerize but condenses with CH3N3 in several steps to produce hexamethylenetetramine. 

N,N -Dinitroso-pentamethylenetetramine exhibits an interesting mechanism of decomposition, which is shown in Figure 21.3. It rearranges thermally into hexamethylenetetramine, which has the famous adamantane structure with e nitrogen and formaldehyde... 

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