Preparation of nitramine-nitrates by ring-opening nitration of aziridines by dinitrogen pentoxide (N2O5
作者:Peter Golding、Ross W Millar、Norman C Paul、David H Richards
DOI:10.1016/s0040-4020(01)87980-1
日期:1993.8
bearing various types of substituents on the ring nitrogen, were treated with N2O5 in chlorinated solvents at sub-ambient temperature and formed 1,2-nitramine-nitrate products by a novel ring-opening nitration reaction analogous to that established for the corresponding oxygen heterocycles (epoxides). A wide variety of classes of aziridine underwent the reaction (N-alkyl, N-(nitroaryl), N-acyl and N-imidyl)
在环境温度下,在氯化溶剂中用N 2 O 5处理13个在环氮上带有各种取代基的氮丙啶,并通过类似于所建立的新型开环硝化反应,形成1,2-硝胺硝酸盐产物。相应的氧杂环(环氧化物)。各种类型的氮丙啶进行了反应(N-烷基,N-(硝基芳基),N-酰基和N-亚氨基),尽管在一种情况下,收率很高(70-82%) N-(烷基羰基)氮丙啶竞争的脱酰反应导致产率降低。另外,带有氮丙啶的基团能够通过N 2 O 5释放硝酸 由于竞争性反应(主要是聚合/低聚),因此(即具有O = H,N = H或未取代的芳基的化合物)大大降低了硝酸硝胺的收率。