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Energetic Materials from Cubane.

ADA160966

Publication Date	1985
Personal Author	Eaton, P. E.
Page Count	23
Abstract	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-bis(N,N-diisopropylcarboxamido)cubane, the first tetrasubstituted cubane.
Keywords	Synthesis(Chemistry) Cyclic compounds Substitution reactions Nuclear structure Energetic properties Heat of formation High density Lithium Mercury Iodine Amides Nitro radicals Organometallic compounds Cubanes Cubane/diiodo-bis(N-N-diisopropylcarboxamido)
Source Agency	Non Paid ADAS
NTIS Subject Category	99D - Basic & Synthetic Chemistry 79A - Ammunition, Explosives, & Pyrotechnics
Corporate Authors	Chicago Univ., IL. Dept. of Chemistry.
Document Type	Technical Report
Title Note	Interim rept. 1 Aug 84-31 Jul 85.
NTIS Issue Number	198604
Contract Number	N00014-84-K-0645

Energetic Materials from Cubane.

Energetic Materials from Cubane.
ADA160966

Publication Date	1985
Personal Author	Eaton, P. E.
Page Count	23
Abstract	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-bis(N,N-diisopropylcarboxamido)cubane, the first tetrasubstituted cubane.
Keywords	Synthesis(Chemistry) Cyclic compounds Substitution reactions Nuclear structure Energetic properties Heat of formation High density Lithium Mercury Iodine Amides Nitro radicals Organometallic compounds Cubanes Cubane/diiodo-bis(N-N-diisopropylcarboxamido)
Source Agency	Non Paid ADAS
NTIS Subject Category	99D - Basic & Synthetic Chemistry 79A - Ammunition, Explosives, & Pyrotechnics
Corporate Authors	Chicago Univ., IL. Dept. of Chemistry.
Document Type	Technical Report
Title Note	Interim rept. 1 Aug 84-31 Jul 85.
NTIS Issue Number	198604
Contract Number	N00014-84-K-0645