Nitration by oxides of nitrogen, part 4: Unexpected behaviour of certain aziridines and azetidines upon reaction with dinitrogen pentoxide

Article abstract of DOI:10.1016/S0040-4039(00)93514-7

Seven aziridines and azetidines, either unsubstituted on ring nitrogen or bearing N-acyl (N,N-dimethylcarbamyl or propionyl) groups, were reacted with N₂O₅ in halogenated solvents with the following results:- the behaviour of the aziridines was highly dependent on the N-substituent, giving respectively dinitrate esters, nitramine-nitrate or predominantly uncharacterisable products, whereas the azetidines gave in all cases N-nitroazetidine. The different behaviour is believed to result from ring strain effects.