Preparation of Di- and polynitrates by ring-opening nitration of epoxides by dinitrogen pentoxide (N2O5)

Article abstract of DOI:10.1016/S0040-4020(01)87978-3

Eighteen epoxides of various kinds were reacted with N₂O₅ in chlorinated hydrocarbon solvents (principally CH₂Cl₂) to give vicinal nitrate ester products by a novel ring-opening nitration reaction. The procedure offers easier temperature control and simpler isolation procedures compared with conventional mixed acid nitrations; it also enables selective nitration reactions to be carried out on polyfunctional substrates. The scope and limitations of the reaction, as well as those of an alternative route utilising N₂O₄ with in situ oxidation of an intermediate nitrite-nitrate, are discussed.