Energetic Materials from Cubane.
Interim rept. 1 Aug 84-31 Jul 85,
CHICAGO UNIV IL DEPT OF CHEMISTRY
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Cubanes are exceptionally strained compounds with high heats of formation. They are also very dense. The combination of these two properties along with proper substituents on the cubane nucleus should lead to highly energetic materials useful as explosives and propellant additives. Cubane-1,4-dicarboxylic acid can be fairly easily prepared from readily available starting materials however, the methodology for the preparation of more highly substituted cubanes--those necessary for the proposed use--has not yet been developed. It is the purpose of this project to develop and investigate approaches to such highly substituted cubanes. This progress report describes work accomplished during the first year of the contract. Before starting on the present contract, we had discovered that it was possible to use amide groups on the cubane nucleus to activate adjacent positions for lithiation. Further, we had shown that such ortho-lithiated cubanes could be intercepted with mercury salts to produce cubyl mercurials. The carbon-mercury bond in such compounds was shown to be reactive toward iodine the final result being the production of cubyl iodides. Thus, as shown in the overall scheme illustrated overleaf, we succeeded in preparing and characterizing 2,7-diiodo-1,4-bisN,N-diisopropylcarboxamidocubane, the first tetrasubstituted cubane.
- Organic Chemistry