Aziridines ring-opening nitration

A number of nitramine-nitrate explosives have been prepared by Millar and co-workers from the action of dinitrogen pentoxide on aziridines and azetidines (Section 5.8). Millar and co-workers used their aziridine ring-opening nitration methodology (Section 5.8.1) to synthesize the high performance melt-castable nitramine-nitrate explosive known as Tris-X... 

Nitration of I-substituted azetidines with N2Os often gives ring-opened products similar to those found for aziridines (95T5073). However, V-acyl azetidines undergo nitrolysis of the substituent to yield /V-nitroazetidines in good yields. 

Ammonium hexanitratocerate(IV) can be used as a catalyst for the ring opening of epoxides in presence of water, thiols or acetic acid (scheme 21) (Iranpoor et al., 1991). Epoxides react in presence of an excess of nitrate ions and a catalytic amount of ammonium hexanitra-tocerate(IV) in acetonitrile to /3-nitrato alcohols (Iranpoor and Salehi, 1995). A combination of ammonium hexanitratocerate(IV) and A-bromosuccinimide (NBS) transforms epoxides into a-hydroxy ketones (scheme 22) (Surendra et al., 2005). Aziridines give a-aminoketones under the same conditions. 

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