Reviews and Accounts
ARKIVOC 2015 (i) 97-135
1,4-Dinitro-1H-imidazoles Jerzy W. Suwiński Centre of Polymer and Carbon Materials, Polish Academy of Sciences, M. Curie-Skłodowskiej 34, Zabrze 41-819, Poland E-mail: jsuwinski@cmpw-pan.edu.pl DOI: http://dx.doi.org/10.3998/ark.5550190.p008.815 Abstract The synthesis, properties, and reactions of 1,4-dinitro-1H-imidazoles as well as the hazards associated with working with them are comprehensively reviewed. Keywords: Imidazoles, nitration, cine substitution, ANRORC reactions
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Introduction Synthesis of 1,4-Dinitro-1H-imidazoles 2.1. Nitration of 4(5)-Nitro-1H-imidazole in Acetic Anhydride–Acetic acid Mixtures 2.2. Nitration of imidazole by nitronium tetrafluoroborate 2.3. Kyodai nitration of imidazole 2.4. “Green nitration” of 4(5)-nitro-1H-imidazole Properties of 1,4-Dinitro-1H-imidazoles 3.1. Common physicochemical and spectroscopic properties 3.2. Potential explosive properties 3.3. Harmfulness depending on the crystalline form Reactions of 1,4-Dinitro-1H-imidazoles 4.1. Thermal rearrangement 4.2. Nucleophilic cine-substitution 4.3. ANRORC Reactions 4.3.1. Reactions with aromatic primary amines 4.3.2. Reactions with compounds containing a primary amino group linked to an aliphatic carbon atom 4.3.3. Reactions with amino derivatives of sugars or nucleosides 4.4. Disproportionation in hot sulfuric acid 4.5. 1-Denitration
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