1968
DOI: 10.1021/jo01267a109
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Reinvestigation of the orientation of halogen substitution in imidazoles by nuclear magnetic resonance spectroscopy

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Cited by 24 publications
(16 citation statements)
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“…Thus, in [81,82] 4(5)-iodoimidazole 157 and not 2-iodoimidazole 145, as previously considered [77], was obtained by the reduction of the triiodide 155 with Na 2 SO 3 according to the method in [77]. It was demonstrated [82] that the 4,5-diiodo derivative 158 and not the 2,4(5)-diiodo derivative 154 was formed during the iodination of imidazole under the previously described conditions [77][78][79] The structure of compounds 157 and 158 was proved rigorously by means of the 1 H NMR spectra [81,82], mass spectra [83], and chemical transformations to 4(5)-iodo-5(4)-nitroimidazole 159 during the nitration of iodoimidazole 157 [84] and ipso nitration of diiodoimidazole 158 [85,86].…”
Section: Synthesis Of 4(5)-iodo- 45-diodo- 245-triiodo- and 12mentioning
confidence: 97%
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“…Thus, in [81,82] 4(5)-iodoimidazole 157 and not 2-iodoimidazole 145, as previously considered [77], was obtained by the reduction of the triiodide 155 with Na 2 SO 3 according to the method in [77]. It was demonstrated [82] that the 4,5-diiodo derivative 158 and not the 2,4(5)-diiodo derivative 154 was formed during the iodination of imidazole under the previously described conditions [77][78][79] The structure of compounds 157 and 158 was proved rigorously by means of the 1 H NMR spectra [81,82], mass spectra [83], and chemical transformations to 4(5)-iodo-5(4)-nitroimidazole 159 during the nitration of iodoimidazole 157 [84] and ipso nitration of diiodoimidazole 158 [85,86].…”
Section: Synthesis Of 4(5)-iodo- 45-diodo- 245-triiodo- and 12mentioning
confidence: 97%
“…Thus, as a result of the repeated investigations [81][82][83][84][85][86][87] it was established that the iodination of imidazole takes place through the same stages as its chlorination and bromination. The only difference lies in the fact that with an excess of iodine the triiodoimidazole 155 also undergoes iodination at position 1 with the formation of the tetraiodoimidazole 156.…”
Section: Synthesis Of 4(5)-iodo- 45-diodo- 245-triiodo- and 12mentioning
confidence: 98%
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“…In the 1 H NMR spectra of the haloimidazoles [3,[14][15][16] and also in other 4,5-substituted imidazoles [17], differences are observed in the chemical shifts of the protons at positions 2 and 4(5) of the heterocycle. Thus, the signal for the H-2 proton is recorded in the region of 7.03-7.91 ppm, while the signals of the H-4 and H-5 protons are upfield in the region of 6.47-7.28 ppm (Table 4).…”
mentioning
confidence: 97%