Preparation and structure of novel hexaazaisowurtzitane cages.
Hexaazaisowurtzitane or cage molecules have attracted attention concerning their synthesis because hexanitrohexaazaisowurtzitane (HNIW or CL20) is presently the most powerful energetic compound. The synthesis of hexaazaisowurtzitanes was considered to be limited solely to the condensation of certain benzylamines with glyoxal. Here, we present the synthesis and characterization of seven novel non-benzylic hexaazaisowurtzitanes, such as hexapropargylhexaazaisowurtzitane. The substituents on the six nitrogen atoms are different to those of the benzyl or substituted benzyl groups to which previous syntheses were limited. X-ray structures are given for the hexapropargyl and hexa-2-thienylmethylene derivatives. Steric strains limit the synthesis with alpha-substituted benzyl and allyl derivatives. The reaction mechanism and the role of the intermediate diimines are discussed. Some of the novel hexaazaisowurtzitanes are potential precursors of hexanitrohexaazaisowurtzitane.
Herve
Grégoire
G
Energetic Molecule Synthesis Laboratory, SNPE Matériaux Energétiques (SME), SNPE Group, Centre de recherches du Bouchet, 9, rue Lavoisier, 91710 Vert-le-Petit, France. g.herve@snpe.com
Jacob
Guy
G
Gallo
Roger
R