Two intermediates, 1,5-dinitroso-3,7-dinitro-1,3,5,7-tetraazacyclooctane (DNDS) and 1-nitroso-3,5,7-trinitro-1,3,5,7-tetraazacyclooctane (MNX), were isolated and characterized in the synthesis of 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane (HMX) from the nitrolysis of 3,7-dinitro-1,3,5,7-tetraazabicyclo[3,3,1]nonane (DPT) for the first time. When the nitrolysis of DPT was slowed down, two intermediates were detected with HPLC. It was proposed that electrophilic NO2+ and NO+ from HNO3 and N2O4 might attack nitrogen atoms at positions 3 and 7 of DPT to form the cations of the intermediates, then nucleophilic H2O attacked the bridge carbon atoms of DPT to produce the intermediates, which were oxidized to form HMX.

中文翻译：

---

3,7-二硝基-1,3,5,7-四氮杂双环[3,3,1]壬烷的硝解机理

两种中间体，1,5-二亚硝基-3,7-二硝基-1,3,5,7-四氮杂环辛烷 (DNDS) 和 1-亚硝基-3,5,7-三硝基-1,3,5,7-四氮杂环辛烷 ( MNX)，在从 3,7-二硝基-1,3,5,7 硝化合成 1,3,5,7-四硝基-1,3,5,7-四氮杂环辛烷 (HMX) 中被分离和表征-四氮杂双环[3,3,1]壬烷（DPT）首次出现。当 DPT 硝化减慢时，HPLC 检测到两种中间体。提出HNO3和N2O4的亲电NO2+和NO+可能攻击DPT的3和7位的氮原子形成中间体的阳离子，然后亲核H2O攻击DPT的桥碳原子产生中间体，中间体被氧化成形成 HMX。