The reaction rates for the rearrangement of eleven(Z)-arylhydrazones of 5-amino-3-benzoyl-1,2,4-oxadiazole 3a-kinto the relevant (2-aryl-5-phenyl-2H-1,2,3-triazol-4-yl)ureas4a-k in the presence of trichloroacetic acid or of piperidinehave been determined in toluene at 313.1 K. The results havebeen related to the effect of the aryl substituent by usingHammett and/or Ingold-Yukawa-Tsuno correlations andhave been compared with those previously collected in a proticpolar solvent (dioxane/water) as well as with those on theanalogous rearrangement of the corresponding (Z)-arylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazole 1a-k in benzene. Some light can thus be shed on the general differences of chemical reactivity between protic polar (or dipolar aprotic) and apolar solvents.

Acid- and Base-Catalysis in the Mononuclear Rearrangement of Some (Z)-Arylhydrazones of 5-Amino-3-benzoyl-1,2,4-oxadiazole in Toluene: Effect of Substituents on the Course of Reaction / F., D’Anna; V., Frenna; Ghelfi, Franco; S., Marullo; D., Spinelli. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 76:8(2011), pp. 2672-2679. [10.1021/jo200066n]

Acid- and Base-Catalysis in the Mononuclear Rearrangement of Some (Z)-Arylhydrazones of 5-Amino-3-benzoyl-1,2,4-oxadiazole in Toluene: Effect of Substituents on the Course of Reaction

GHELFI, Franco;
2011

Abstract

The reaction rates for the rearrangement of eleven(Z)-arylhydrazones of 5-amino-3-benzoyl-1,2,4-oxadiazole 3a-kinto the relevant (2-aryl-5-phenyl-2H-1,2,3-triazol-4-yl)ureas4a-k in the presence of trichloroacetic acid or of piperidinehave been determined in toluene at 313.1 K. The results havebeen related to the effect of the aryl substituent by usingHammett and/or Ingold-Yukawa-Tsuno correlations andhave been compared with those previously collected in a proticpolar solvent (dioxane/water) as well as with those on theanalogous rearrangement of the corresponding (Z)-arylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazole 1a-k in benzene. Some light can thus be shed on the general differences of chemical reactivity between protic polar (or dipolar aprotic) and apolar solvents.
2011
76
8
2672
2679
Acid- and Base-Catalysis in the Mononuclear Rearrangement of Some (Z)-Arylhydrazones of 5-Amino-3-benzoyl-1,2,4-oxadiazole in Toluene: Effect of Substituents on the Course of Reaction / F., D’Anna; V., Frenna; Ghelfi, Franco; S., Marullo; D., Spinelli. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 76:8(2011), pp. 2672-2679. [10.1021/jo200066n]
F., D’Anna; V., Frenna; Ghelfi, Franco; S., Marullo; D., Spinelli
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/649101
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