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Title: Synthesis and characterization of multicyclic oxadiazoles and 1-hydroxytetrazoles as energetic materials

Abstract

Synthesis and characterization of several multicyclic oxadiazoles, 3,5-bis(4-nitrofurazan-3-yl)-1,2,4-oxadiazole, 3,3'-bis(4-nitrofurazan-3-yl)-5,5'-bi(1,2,4-oxadiazole), 3-(4-nitrofurazan-3-yl)-1,2,4-oxadiazol-5-amine, and salts of 1-hydroxytetrazoles, ammonium 5,5'-(1,2,4-oxadiazole-3,5-diyl)bis(1H-tetrazol-1-olate) and hydroxylammonium 5,5'-{[3,3'-bi(1,2,4-oxadiazole)]-5,5'-diyl}bis(1H-tetrazol-1-olate), as energetic materials are reported here. Two of the compounds, 3,5-bis(4-nitrofurazan-3-yl)-1,2,4-oxadiazole and 3,3'-bis(4-nitrofurazan-3-yl)-5,5'-bi(1,2,4-oxadiazole), have attractive single crystal densities of 1.91 and 1.94 g·cm –3 (at 20°C), respectively. The design of these materials has been based on the idea that these multicyclic compounds with a 1,2,4-oxadiazole core will have good thermal stability and high density because of their 3,5-substitution pattern and the possibility of achieving a planar conformation. The various synthetic approaches and interesting chemistry observed during the construction of these new heterocycles has been described.

Authors:
 [1];  [1];  [1];  [1];  [2]
  1. Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
  2. Naval Research Lab. (NRL), Washington, DC (United States)
Publication Date:
Research Org.:
Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States); Naval Research Lab. (NRL), Washington, DC (United States)
Sponsoring Org.:
USDOE National Nuclear Security Administration (NNSA); USDOD
OSTI Identifier:
1524284
Report Number(s):
LLNL-JRNL-720247
Journal ID: ISSN 0009-3122; 865679
Grant/Contract Number:  
AC52-07NA27344
Resource Type:
Accepted Manuscript
Journal Name:
Chemistry of Heterocyclic Compounds
Additional Journal Information:
Journal Volume: 53; Journal Issue: 6-7; Journal ID: ISSN 0009-3122
Publisher:
Springer
Country of Publication:
United States
Language:
English
Subject:
furazans; 1-hydroxytetrazoles; nitroheterocycles; 1,2,4-oxadiazoles; tetrazoles; energetic materials

Citation Formats

Pagoria, Philip F., Zhang, Mao-Xi, Zuckerman, Nathaniel B., DeHope, Alan J., and Parrish, Damon A. Synthesis and characterization of multicyclic oxadiazoles and 1-hydroxytetrazoles as energetic materials. United States: N. p., 2017. Web. doi:10.1007/s10593-017-2122-9.
Pagoria, Philip F., Zhang, Mao-Xi, Zuckerman, Nathaniel B., DeHope, Alan J., & Parrish, Damon A. Synthesis and characterization of multicyclic oxadiazoles and 1-hydroxytetrazoles as energetic materials. United States. doi:10.1007/s10593-017-2122-9.
Pagoria, Philip F., Zhang, Mao-Xi, Zuckerman, Nathaniel B., DeHope, Alan J., and Parrish, Damon A. Thu . "Synthesis and characterization of multicyclic oxadiazoles and 1-hydroxytetrazoles as energetic materials". United States. doi:10.1007/s10593-017-2122-9. https://www.osti.gov/servlets/purl/1524284.
@article{osti_1524284,
title = {Synthesis and characterization of multicyclic oxadiazoles and 1-hydroxytetrazoles as energetic materials},
author = {Pagoria, Philip F. and Zhang, Mao-Xi and Zuckerman, Nathaniel B. and DeHope, Alan J. and Parrish, Damon A.},
abstractNote = {Synthesis and characterization of several multicyclic oxadiazoles, 3,5-bis(4-nitrofurazan-3-yl)-1,2,4-oxadiazole, 3,3'-bis(4-nitrofurazan-3-yl)-5,5'-bi(1,2,4-oxadiazole), 3-(4-nitrofurazan-3-yl)-1,2,4-oxadiazol-5-amine, and salts of 1-hydroxytetrazoles, ammonium 5,5'-(1,2,4-oxadiazole-3,5-diyl)bis(1H-tetrazol-1-olate) and hydroxylammonium 5,5'-{[3,3'-bi(1,2,4-oxadiazole)]-5,5'-diyl}bis(1H-tetrazol-1-olate), as energetic materials are reported here. Two of the compounds, 3,5-bis(4-nitrofurazan-3-yl)-1,2,4-oxadiazole and 3,3'-bis(4-nitrofurazan-3-yl)-5,5'-bi(1,2,4-oxadiazole), have attractive single crystal densities of 1.91 and 1.94 g·cm–3 (at 20°C), respectively. The design of these materials has been based on the idea that these multicyclic compounds with a 1,2,4-oxadiazole core will have good thermal stability and high density because of their 3,5-substitution pattern and the possibility of achieving a planar conformation. The various synthetic approaches and interesting chemistry observed during the construction of these new heterocycles has been described.},
doi = {10.1007/s10593-017-2122-9},
journal = {Chemistry of Heterocyclic Compounds},
number = 6-7,
volume = 53,
place = {United States},
year = {2017},
month = {6}
}

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Works referenced in this record:

New synthesis of 1,2,4-oxadiazoles
journal, January 1990


Synthesis and properties of 4-amino-3-cyanofurazan
journal, May 1994

  • Andrianov, V. G.; Eremeev, A. V.
  • Chemistry of Heterocyclic Compounds, Vol. 30, Issue 5, p. 608-611
  • DOI: 10.1007/BF01169844