2004
DOI: 10.1016/j.tet.2003.12.007
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Dynamic 1H NMR study of 4-methylphenoxyimidoyl azides: conformational or configurational isomerisation?

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Cited by 33 publications
(17 citation statements)
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“…Ab initio, AM1 and PM3 calculations of 1 complement the X-ray findings and demonstrate that the dioxane ring adopts a chair conformation, that the imidoyl amino group prefers an axial conformation and that the tosyl and tolyl groups about the C=N bond retain an E configuration. We have recently reported a similar phenomenon for compound 2 [60]. The results of this investigation demonstrate that ab initio, AM1 and PM3 calculations are consistent with the findings of MM2 and X-ray in defining the anomeric effect, conformation, configuration and structure of N-2-(1,4-dioxane)-N'-(4-methylbenzenesulfonyl)-O-(4-methylphenoxy) isourea.…”
Section: Resultssupporting
confidence: 87%
“…Ab initio, AM1 and PM3 calculations of 1 complement the X-ray findings and demonstrate that the dioxane ring adopts a chair conformation, that the imidoyl amino group prefers an axial conformation and that the tosyl and tolyl groups about the C=N bond retain an E configuration. We have recently reported a similar phenomenon for compound 2 [60]. The results of this investigation demonstrate that ab initio, AM1 and PM3 calculations are consistent with the findings of MM2 and X-ray in defining the anomeric effect, conformation, configuration and structure of N-2-(1,4-dioxane)-N'-(4-methylbenzenesulfonyl)-O-(4-methylphenoxy) isourea.…”
Section: Resultssupporting
confidence: 87%
“…An advantage of tetrazolic acids over carboxylic aids is that, they are resistant to many biological metabolic degradation path ways 3–5. Another important application of tetrazoles is in the preparation of imidoylazides 12, 13. Also tetrazoles have found use in pharmaceuticals,14 specialty explosives,15 photography, and information recording systems,16 not to mention as precursor to a variety of nitrogen containing heterocycles 17, 18…”
Section: Introductionmentioning
confidence: 99%
“…8c The addition of azide anion to nitriles, cyanates and cyanamides is the most common direction for preparing 5-substituted tetrazoles and 5-aryl/alkyl oxytetrazoles. [10][11] In most cases, reaction actually proceeds in solutions of hydrazoic acid in solvents such as benzene, toluene, xylene and chloroform. When hydrazoic acid is used, care must be taken by monitoring the concentration of hydrazoic acid in the reaction mixture to avoid an explosion.…”
Section: Introductionmentioning
confidence: 99%