THE NITROLYSIS OF HEXAMETHYLENETETRAMINE: IV. SYNTHESIS OF A CYCLONITE HOMOLOGUE

A homologue of Cyclonite has been prepared. This homologue, 1,3,6-trinitro-1,3,6-triazacycloheptane was formed by nitrolysis of methylene-bis-3,6-dinitro-1,3,6-triazacycloheptane, which was synthesized from N,N′-dimethylol-1,2-dinitraminoethane, formaldehyde, and ammonia. The reliability of this synthesis was established by analogous reactions. The nitrolysis yields also 1,8-diacetoxy-2,4,7-trinitro-2,4,7-triazaöctane via 1-acetoxymethyl-3,6-dinitro-1,3,6-triazacycloheptane. Ammonium nitrate has been shown to promote demethylolation in this series just as it does in the triazacyclohexane compounds. Analogies have therefore been drawn between these nitrolyses and that of hexamethylene-tetramine. Further comparisons derive from the isolation of 1-acetoxymethyl-3,6-dinitro-1,3,6-triazacycloheptane and 1-aceto-3,6-dinitro-1,3,6-triazacycloheptane by acetolysis of methylene-bis-dinitrotriazacycloheptane with acetic anhydride.