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Synlett 2013; 24(4): 519-521
DOI: 10.1055/s-0032-1318142
letter
© Georg Thieme Verlag Stuttgart · New York

Nucleophilic Reactions of The Bis Ammonium Salt of 4,4′,5,5′-Tetranitro-2,2′-biimidazole

Megan M. Breiner
a   Los Alamos National Laboratory, Weapons Experiments Division, Los Alamos, NM 87545, USA   Fax: +1(505)6670500   Email: dechavez@lanl.gov
,
David E. Chavez*
a   Los Alamos National Laboratory, Weapons Experiments Division, Los Alamos, NM 87545, USA   Fax: +1(505)6670500   Email: dechavez@lanl.gov
,
Damon A. Parrish
b   Naval Research Laboratory, Laboratory for the Structure of Matter, Washington, DC 20375, USA
› Author Affiliations
Further Information

Publication History

Received: 10 December 2012

Accepted after revision: 10 January 2013

Publication Date:
29 January 2013 (online)

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Abstract

The reactivity of the bis ammonium salt of 4,4′,5,5′-tetranitro-1,1′-biimidazole toward nucleophilic addition to the electrophiles dimethylsulfate and mesitylene-O-sulfonyl hydroxylamine has been studied. We have found that the tetranitrobiimidazolate bis anion has sufficient nucleophilicity to react with these electrophiles to form new products, 1,1′-dimethyl-4,4′,5,5′-tetranitro-2,2′-biimidazole (DMTNBI), 1,1′-diamino-4,4′,5,5′-tetranitro-2,2′-biimidazole, and ammonium 1-amino-4,4′,5,5′-tetranitro-2,2′-biimidazolate. These materials were characterized chemically and with respect to their thermal stability.

Key words

biimidazoles - heterocycles - N-amination - explosives - nitro compounds

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