Synthesis of 2-Nitroimino-5-Nitrohexahydro-1,3,5-Triazinevia Chloride-Assisted Nitrolysis of a Tertiary Amine

Autor:	Robert P. Parker, Gene Walker, Matthew D. Cliff, Ian J. Dagley
Rok vydání:	1998
Předmět:	Chloramine Tertiary amine General Chemical Engineering General Chemistry Nitrolysis Chloride chemistry.chemical_compound chemistry 1 3 5-Triazine Nitration Yield (chemistry) Polymer chemistry medicine Moiety Organic chemistry medicine.drug
Zdroj:	Propellants, Explosives, Pyrotechnics. 23:179-181
ISSN:	1521-4087 0721-3115
Popis:	An alternative synthesis of the insensitive energetic nitramine 2-nitroimino-5-nitrohexahydro-1,3,5-triazine (1) via nitrolysis of a tertiary amine is presented. Nitration of the tertiary amine precursor (2) is effected by chloride-assisted elimination of the tert-butyl moiety, with the chloramine presumably formed as an intermediate. The reaction fails to proceed in the absence of chloride at 0°C, however, its inclusion in the reaction system leads to a smooth conversion to (1) under mild nitrating conditions, which can be scaled up to yield multigram quantities. This is the first known example of a chloride-assisted nitrolysis of a tertiary amine to appear in the open literature.
Databáze:	OpenAIRE
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