6533b85dfe1ef96bd12be00a
RESEARCH PRODUCT
Unexpected Substituent Effects in the Iso-Heterocyclic Boulton-Katritzky Rearrangement of 3-Aroylamino-5-methyl-1,2,4-oxadiazoles: A Mechanistic Study.
Domenico SpinelliAntonio Palumbo-piccionelloPaolo Lo MeoVincenzo Frennasubject
010304 chemical physicsChemistryKineticsSubstituent124-oxadiazoleSettore CHIM/06 - Chimica OrganicaMononuclear Heterocyclic Rearrangement010402 general chemistry01 natural sciences0104 chemical sciencesKineticschemistry.chemical_compoundSubstituent effectComputational chemistry0103 physical sciencesPhysical and Theoretical ChemistryReaction mechanismdescription
The kinetics of the iso-heterocyclic mononuclear rearrangement of some 3-aroylamino-5-methyl-1,2,4-ozadiazoles was carefully examined under largely variable acidic or alkaline conditions. This reaction may proceed via two different mechanistic pathways (an uncatalyzed and a base-catalyzed one), as accounted for also by the evaluation of the relevant activation parameters. Substituent effects, as quantified by means of the Hammett’s equation, appear relatively modest; however, they reveal some interesting anomalies, which enabled us to draw a very precise picture of the intimate reaction course.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2019-10-17 | The journal of physical chemistry. A |