Aziridines reactions with dinitrogen pentoxide

Research efforts are ongoing into the use of dinitrogen pentoxide for the industrial synthesis of nitrated hydroxy-terminated polybutadiene (NHTPB) from epoxidated HTPB (Section 3.10). The reaction of aziridines with dinitrogen pentoxide is an important route to 1,2-nitramine-niU ates and these reactions are discussed in Section 5.8.1. ... 

Millar and co-workers studied the reaction of dinitrogen pentoxide in chlorinated solvents with a number of different A-substituted aziridines and found that reactions are highly dependent on the nature of the A-substituent on the aziridine nitrogen (Table 5.9). A-Alkylaziridines give good yields of 1,2-nitramine-nitrate product (Table 5.9, Entry 1). These... 

Nitramine-nitrates from the reaction of aziridines with dinitrogen pentoxide (ref. 124)... 

The reaction of azetidines with dinitrogen pentoxide is found to reflect the reduced ring strain in this system compared to aziridines.Accordingly, while the carbamate and V-alkyl... 

The reaction of aziridines and azetidine heterocycles with dinitrogen pentoxide in chlorinated solvents yields 1,2-nitramine nitrates and 1,3-nitramine nitrates respectively. In most cases yields are good to excellent, but, reactions are not as general as with the oxygen heterocycles the outcome of reactions is heavily dependent on the nature of the substituent on the exocyclic nitrogen. Some of the products from these reactions find use as melt-castable explosives i.e. Tris-X (46) and energetic plasticizers e.g. Bu-NENA (48) the latter is a component of some LOVA (low vulnerability ammunition) propellant formulations. 

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