Tetrahedron p. 7037 - 7050 (1993)
Update date:2022-08-05
Topics: Preparation Epoxides Dinitrogen pentoxide (N2O5) Ring-opening nitration Diand polynitrates
Golding, Peter
Millar, Ross W.
Paul, Norman C.
Richards, David H.
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.
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