The N-nitroxymethyl derivatives of 1,3-dinitroperhydro-1,3,5-triazine, piperidine, and succinimide
N-Nitroxymethylpiperidine and N-nitroxymethylsuccinimide have been prepared and their reactions with nucleophiles and nitric acid under various conditions have been compared. Their relative reactivities have been explained in terms of the degree of carbonium ionic character of the methylenic carbon atom attached to the nitroxy-group. 1,3-Dinitro-5-nitroxymethylperhydro-1,3,5-triazine has eluded preparation from either (a) the N-acetoxymethyl analogue with nitric acid in acetonitrile or (b) the N-chloromethyl analogue with silver nitrate also in acetonitrile. In case (a) an interaction with the solvent is explained and in case (b) the formation of the bicyclic nitramine 1,5-bis-(3,5-dinitroperhydro-1,3,5-triazin-1-yl)-2,4-dinitro-2,4-diazapentane has been proved.