
TY  - JOUR
A1  - Grimmett, MR 
A1  - Hua, ST 
A1  - Chang, KC 
A1  - Foley, SA 
A1  - Simpson, J 
T1  - 1,4-Dinitroimidazole and Derivatives. Structure and Thermal Rearrangement
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1989
VL  - 42
IS  - 8
SP  - 1281
EP  - 1289
KW  - 
UR  - https://doi.org/10.1071/CH9891281 
N2  - 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. 
ER  -

