Reactions of primary and secondary amines with N-nitrosuccinimide

ORGN 110

Qi-Li Feng, fengqili@yahoo.com.cn, The Key Laboratory of Food Science of MOE, Department of Food Science and Technology, Nanchang University, Nanchang 330047, China
N-Nitramides and N-nitramines are known to undergo various unexpected and new reactions, many of which are synthetically useful and mechanistically interesting. Examples of such reactions include intermolecular transfer reactions of the N-nitro group, the thermal intramolecular rearrangement of the N-nitro group to a carbon atom. In our continuing studies on the chemistry of N-nitramide, facile reactions of N-nitrosuccinimide with a variety of primary and secondary amines are uncovered to provide crystalline ammonium salts. Upon treated at elevated temperatures, the salts are transformed into symmetric di-amides.