Polycyclic N-Oxides as High-Performance Energetic Materials

  • Author: ChemistryViews.org
  • Published: 30 January 2019
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Chemical Communications/Royal Society of Chemistry
  • Associated Societies: Royal Society of Chemistry (RSC), UK
thumbnail image: Polycyclic N-Oxides as High-Performance Energetic Materials

Polycyclic compounds often stack very efficiently in crystals due to interactions between their π-electron systems. This can be useful for the development of energetic materials (explosives, propellants, etc.), which usually require a high density for good performance.

Christopher J. Snyder, David E. Chavez, Los Alamos National Laboratory, NM, USA, and colleagues have developed polycyclic N-oxides based on 1,2,4,5-tetrazine and 4H,8H-difurazano[3,4-b:3',4'-e]pyrazine (DFP), which can be used as energetic materials. The team performed an addition reaction between DFP as a nucleophile and 3-chloro-6-(3',5'-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine as an electrophile in different ratios to give 1:2 or 1:1 adducts. These intermediates were then treated with ammonia and finally oxidized using peroxytrifluoroacetic acid (PTFA) to give the desired products (example pictured based on 1:1 adduct).

The synthesized polycyclic N-oxides were found to be less sensitive to impact and friction than the widely used explosive RDX (cyclotrimethylenetrinitramine). They also have excellent thermal stabilities and detonation performances. According to the researchers, the sensitivity and detonation properties of the materials can be tuned by varying the size of the polycyclic N-oxide system.


Article Views: 909

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter

A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH