Diazepines. Part XX. The properties of 2,3-dihydro-1,4-diazepinium perchlorate

Abstract

The unsubstituted 2,3-dihydro-1,4-diazepinium ion shows a number of differences from the substituted derivatives studied hitherto. Although it undergoes halogenation at position 6, it cannot be nitrated by nitric acid and is decomposed by mineral acids. The ring is also opened by the action of nucleophiles at the 5- and 7-positions. A transdiazepination reaction occurs with NN′-dimethylethylenediamine to give the NN′-dimethyldihydrodiazepinium salt. 6-Halogeno-derivatives do not react at the 6-position with nucleophiles.