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Paper | Regular issue | Vol 48, No. 4, 1998, pp.657-669
Published online, 1st January, 1970
DOI: 10.3987/COM-97-8027
Chloride-assisted Nitrolysis of Cyclic Tertiary Amines

Matthew D. Cliff

*Aeronautical and Maritime Research Laboratory, Deffence Science and Technology Organisation, P.O. Box 1500, Salisbury, SA 5108, Australia


The synthesis of nitramines from tertiary amine heterocycles via a chloride-assisted nitrolysis is presented. The process is effective for heterocyclic systems containing a single tertiary amine moiety and gives good to excellent yields for primary, secondary and tertiary alkyl leaving groups. Heterocyclic systems containing two tertiary amines are best nitrated via a tert-butyl leaving group, with other alkyl moieties leading to ring-opened species upon treatment with nitrating media both in the presence and absence of chloride ions.