Research in Energetic Compounds

Abstract

Reaction parameters for the polymerization of 3-azidooxetane, catalyzed by boron trifluoride, were investigated. No significant improvements over the previously attained yields (about 50%) resulted from variations of temperature, catalyst level, water content or the use of 1,4-butanediol as a cocatalyst. Increasing the monomer concentration from 20% to 50%, however, gave 80-90% yields of polymer. 2-Aminoadamantane, prepared from 2-adamantanone and sodium cyanoborohydride, was oxidized to give 2-nitroadamantane. The reaction of 4-bromo-2,2-dinitroadamantane with sodium azide gave 4-azido-2-adamantanone. Nitration of 2,4-adamantanedione dioxime gave the internal nitroso dimer of 2,4- dinitro-2,4-dinitrosoadamantane. Reaction of 2,6-adamantanedione dioxime with NBS gave 2,6-di-bromo-2,6-dinitroadamantane. Debromination with sodium borohydride, followed by nitration with tetranitromethane, gave 2,2,6,6- tetranitro-adamantane. The reaction of bicyclo(3,3,1)nona-2,6-dione dioxime with hypochlorous acid gave a chlorohydrocarbon, but reaction of the dioxime with chlorine gave 2,6-dichloro-2,6-dinitrosobicyclo(3,3,1)nonane. This nitroso compound reacted with hypochlorous acid to give 2,6-dichloro-2,6 dinitrobicyclo(3,3,1)nonane. 2,6-Diaminobicyolo(3,3,1)nonane, obtained from bicyclo(3,3,1)nona-2,6-dione and sodium cyanoborohydride was oxidized to the 2, 6-dinitro derivative.

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Document Details

Document Type
Technical Report
Publication Date
Jan 01, 1983
Accession Number
ADA124911

Entities

People

  • Kurt Baum
  • Thomas C. Archibald

Tags

Communities of Interest

  • Weapons Technologies

DTIC Thesaurus Topics

  • Acids
  • Alkenes
  • Chemical Synthesis
  • Chemistry
  • Chlorides
  • Chlorine
  • Hypochlorous Acid
  • Magnesium Compounds
  • Materials
  • Nitro Compounds
  • Organic Chemistry
  • Polyethylene Glycols
  • Polymerization
  • Sodium
  • Sodium Azides
  • Sodium Compounds
  • Sodium Hydroxide

Fields of Study

  • Chemistry

Readers

  • Neurotoxicology
  • Organic Chemistry