Accession Number : ADA294525

Title :   Reactions of Benzotriazolo(2,1-alpha)benzotriazole Derivatives. I. Synthesis of New Insensitive High Density Energetic Compounds.

Descriptive Note : Technical rept.,

Corporate Author : NEW ORLEANS UNIV LA DEPT OF CHEMISTRY

Personal Author(s) : Subramanian, Ganesan ; Boyer, Joseph H. ; Buzatu, Dan ; Stevens, Edwin D. ; Trudell, Mark L.

PDF Url : ADA294525

Report Date : 03 MAY 1995

Pagination or Media Count : 26

Abstract : The sequential preference of electrophilic attack on the dibenzotetraazapentalene ring system 6 has unequivocally been shown to be in the order of position 2(8) > 4(10) >> 1(7) and 3(9). However, nucleophilic substitution reactions with sodium azide were found to be substrate dependent. Substitution occurred at the 3(9)-position of 9 followed by elimination of hydrogen chloride to give 10 while direct substitution of azide for the 4(10)-nitro group of 2 was found to yield 13. The reactivity of the dibenzotetraazapentalene derivatives toward electrophiles and nucleophiles was exploited for the synthesis of the new heterocyclic system 3,4,9,10-bisfuroxano- 5,1 1-dehydro-5H,11H-benzotriazolo(2,1-alpha)benzotriazole 11. From this study the first of a new class of insensitive energetic materials 4 has been synthesized in a straightforward fashion from 2. jg

Descriptors :   *HIGH DENSITY, *ORGANIC COMPOUNDS, *ENERGETIC PROPERTIES, *NUCLEOPHILIC REACTIONS, VELOCITY, SYNTHESIS, MOLECULES, COMPOSITE MATERIALS, REACTIVITIES, SUBSTRATES, CARBON, EXPLOSIVES, NITROGEN, OXYGEN, CHEMICAL REACTIONS, HEAT, FRICTION, ELIMINATION, SUBSTITUTION REACTIONS, HETEROCYCLIC COMPOUNDS, DETONATION WAVES, HYDROGEN CHLORIDE, SODIUM AZIDES.

Subject Categories : Organic Chemistry
      Inorganic Chemistry
      Physical Chemistry
      Ammunition and Explosives

Distribution Statement : APPROVED FOR PUBLIC RELEASE