Ring-opening nitration of epoxides

2 Vicinal dinitrate esters from the reaction of epoxides with dinitrogen pentoxide 

In many cases almost quantitative yields are reported for the formation of v/c-dinitrate esters from the reaction of simple alkyl and dialkyl epoxides with dinitrogen pentoxide (Table 3.2). Some of the products formed include ethylene glycol dinitrate (2) (96%), 1,2-propanediol dinitrate (8) (96 %), 2,3-butanediol dinitrate (94 %) and 1,2-butanediol dinitrate (96 %). Reaction times are of the order of 5-15 minutes. 

Synthesis of vicinal dInItrate esters from the ring opening nitration of epoxides with dinitrogen pentoxide (Ref. 75)  

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.  

3 Reaction of epoxides with nitrate anion under acidic conditions 

---