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Synthesis 2012(8): 1253-1257  
DOI: 10.1055/s-0031-1289736
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Trinitromethyl- and Dinitromethyl-Substituted Azoles Using Nitrate Salts in Sulfuric Acid

Venugopal Thottempudi, Jean’ne M. Shreeve*
Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA
Further Information

Publication History

Received 1 February 2012
Publication Date:
05 March 2012 (online)

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Abstract

Synthesis of trinitromethyl and dinitromethyl-substituted azoles employing a mild and efficient nitration method has been developed using a mixture of sulfuric acid and an inorganic nitrate salt XNO3, where X = NH4 +, Na+, K+. This methodology exhibits clear advantages over the more popular mixed acids nitration approach. Various nitro functionalities such as C-trinitromethyl, N-trinitromethyl, and dinitromethyl ester containing azoles were prepared in moderate to excellent yields with reduced reaction times using this method.

Key words

nitrate salts - mixed acids - nitration - polynitroazoles - trinitromethyls - energetic materials

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