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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Synthesis and structural characterization of 3,5-dinitro-1,2,4-triazolates

R Haiges1, G Bélanger-Chabot, S M Kaplan

  • 1Loker Hydrocarbon Research Institute, University of Southern California, Los Angeles, CA 90089-1661, USA. haiges@usc.edu.

Dalton Transactions (Cambridge, England : 2003)
|January 24, 2015
PubMed
Summary

Researchers synthesized and characterized salts of 3,5-dinitro-1H-1,2,4-triazole, a key component for energetic materials. Many salts show high thermal stability and low sensitivity, indicating potential for safe and effective energetic material applications.

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Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
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