Novel high-nitrogen materials based on nitroguanyl-substituted tetrazines

Organic Letters

Volumn 6, Issue 17, 2004, Pages 2889-2891

  Chavez, David E ^a   Hiskey, Michael A ^a   Gilardi, Richard D ^b  

^a LOS ALAMOS NATIONAL LABORATORY   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GUANINE DERIVATIVE; NITROGEN; TETRAZINE DERIVATIVE;

ARTICLE; CHEMICAL PROCEDURES; MATERIALS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 4444286246     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049076g     Document Type: Article

References (25)

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20. Compound 1 is prepared on the pound scale in two steps at Los Alamos National Laboratory, starting from acetylacetone and triaminoguanidine hydrochloride. Coburn, M. D.; Buntain, G. A.; Harris, B. W.; Hiskey, M. A.; Lee, K.-Y.; Ott, D. G. J. Heterocycl. Chem. 1991, 28, 2049.
21. Side reactions in a similar system have been described; see ref 7.
22. KOMe was also used as a base and provided the more soluble potassium salt of nitroguanidine. which was an equally effective nucleophile.
23. CCDC 239345 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax (+44)1223-336-033; deposit@ccdc.cam.ac.uk).
24. Dobratz, B. M. Lawrence Livermore National Laboratory Explosives Handbook; Properties of Chemical Explosives and Explosive Simulants; UCRL-52997, National Technical Information Service, U. S. Department of Commerce: Springfield, VA, 1981.
25. Compounds 3-6 are explosives and should be handled appropriately.