
%0 Journal Article
%A Grimmett, MR 
%A Hua, ST 
%A Chang, KC 
%A Foley, SA 
%A Simpson, J 
%T 1,4-Dinitroimidazole and Derivatives. Structure and Thermal Rearrangement
%J Australian Journal of Chemistry
%D 1989/08/01
%V 42
%N 8
%P 1281-1289
%K 
%R https://doi.org/10.1071/CH9891281
%U https://www.publish.csiro.au/paper/CH9891281 
%X Nitration of 4-nitroimidazole in acetic anhydride/glacial acetic acid gives 1,4-dinitroimidazole. The crystal and molecular structure of this compound have been determined by direct methods. Crystals are orthorhombic; P212121, a 5.853(3), b 9.591(8), c 10.392(5) Å , V 583.4(7) Å 3 , Dm 1 .76 g cm-1, Dc, 1 .80 g cm-1 (Z = 4); &#955; 0.71069 Å ; T 173 K. The structure was refined to R = 0.048 for 926 reflections [I > 2 &#963;(1)]. Both 2-methyl-4-nitro- and 5-methyl-4-nitro-imidazoles N-nitrate under the same conditions. When heated in solution at 100-140ºC 1,4-dinitro- and 2-methyl-1,4-dinitro-imidazoles rearrange to give C-nitro isomers and some denitration products, but 5(4)-methyl-1,4(5)-dinitroimidazole failed to give identifiable products. 
