Ring-opening nitration

The product of interaction (possibly an V-nitro and/or ring-opened nitrate ester... 

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

A suspension of thallium (III) nitrate in hexane reacts with epoxides to give the corresponding -hydroxy nitrate esters in good yield. The same reagent in acetonitrile has been used to synthesize a-nitratoketones from substituted acetophenones, 1,2-dinitrate esters from alkenes, and 1,3-dinitrates from ring-opening nitration of cyclopropanes. ... 

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... 

RING-OPENING NITRATION OF STRAINED NITROGEN HETEROCYCLES... 

An example of a ring-opening nitration reaction is shown below. 

Archibald and Manser prepared NF2-substituted analogs of pentaerythrityl esters (such as PETN). Specifically, 3-(difluoraminomethyl)-3-methyloxetane (14) and 3,3-bis(difluoraminomethyl)oxetane (15) [101] were subjected to ring-opening nitration by nitric acid (Scheme 12), giving corresponding 1,3-propanediyl dinitrate esters in quantitative yield [105,106]. As neopentyl difluoramines, the products had superior stabihty compared to many other mono(difluoramino)alkyl-substituted compounds. 2,2-Bis(difluoraminome-thyl)-l,3-propanediyl dinitrate (16) showed a melting point of 58 °C and DSC onset/peak of 177/188 °C. 

---