Nucleophilic Displacements of Imidazoles. I. Oxygen, Nitrogen and Carbon Nucleophiles
- 1 January 1987
- journal article
- research article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 40 (8) , 1399-1413
- https://doi.org/10.1071/ch9871399
Abstract
4(5)-Bromo-and-iodo-imidazoles, activated by an adjacent nitro substituent, undergo nucleophilic displacement with methoxide, phenoxide, cyclic secondary amines and cyanide. The regiochemistry of the reactions of 5-iodo-4-nitroimidazole with methoxide has been confirmed by spectroscopic and X-ray methods, and a number of erroneous structures from the literature have been revised. Some apparently anomalous reactions of methoxide with 5-halo-1,2-dimethyl-4-nitroimidazoles, and cyanide with 4-halo-1-methyl-5-nitroimidazole have been noted. The crystal and molecular structure of 5-methoxy-1-methyl-l4-nitroimidazole has been determined by direct methods. Crystals are monoclinic, P21/c, a 10.929(3), b 8.899(2), c 7.290(2) .ANG.; .beta. 92.87(2).degree.; Z 4. The structure was refined to R = 0.095 for 818 reflections (I > 2 .sigma. I).Keywords
This publication has 3 references indexed in Scilit:
- 4- and 5-nitroimidazoles: 13C NMR assignment of structureTetrahedron, 1983
- The crystal structure of imidazole at 103 K by neutron diffractionActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1979
- O-Methyl [2-(2-ethyl-5-nitroimidazol-1-yl)ethyl]thiocarbamate (sulnidazole)Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1977