Accession Number : ADA189115

Title :   Synthesis of Energetic Materials.

Descriptive Note : Annual progress rept. 1 Jan-31 Dec 86,

Corporate Author : NAVAL SURFACE WEAPONS CENTER SILVER SPRING MD

Personal Author(s) : Chaykovsky, M ; Koppes, W M

PDF Url : ADA189115

Report Date : Mar 1987

Pagination or Media Count : 16

Abstract : The chemistry of the 2,6-diazabicyclooctane ring system was studied toward the synthesis of tetra- and hexa-substituted derivatives. Stable dinitro derivatives were prepared but attempts to prepare tetranitro derivatives by oxidative nitration were unsuccessful, and work on the diazabicyclooctanes was terminated. Methylenedinitramine (MEDINA) was successfully condensed with glyoxal in acetic anhydride to give a substitute dinitroimidazolidine which shows promise as a precursor for the synthesis of bicyclo HMX. Trichloroacetamidine condensed with glyoxal and oxalyl chloride to give a trichloromethyl substituted dihydroxyimidazoline and imidazolinedione respectively. The imidazoline was unstable and could not be converted into the bistrichloromethyl substituted tetraazabicyclooctane ring system for further condensation with trichloroacetamidine. The stable imidazolinedione, on the other hand, is a potential intermediate for such a condensation reaction. Trihalomethyl-bisformamides and bisacetamides are also potential precursors for this substituted bicyclic ring system. The trihalomethyl groups should precursors for this substituted bicyclic ring system. The trihalomethyl groups should stabilize the ring during nitrolysis reactions leading to the bicyclo-HMX system.

Descriptors :   *ENERGETIC PROPERTIES, *MATERIALS, *NITRATION, *OXIDATION, *SYNTHESIS, *SYNTHESIS(CHEMISTRY), *CYCLIC COMPOUNDS, *OCTYL RADICALS, ACETIC ANHYDRIDE, CHEMISTRY, CONDENSATION, CONDENSATION REACTIONS, PRECURSORS, RINGS

Subject Categories : Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE