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Updated: May 1, 2026

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
Understanding the high reactivity of triazolinediones in Diels-Alder reactions. A DFT study
María A Fernández-Herrera1, Claudia Zavala-Oseguera, José Luis Cabellos
1Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, 72570, Puebla, Pue., Mexico, marieta.fernandez@correo.buap.mx.
Abstract:
The participation of 4-substituted-1,2,4-triazoline-3,5-diones (TADs) in Diels-Alder reactions toward a series of dienes is studied at the M05-2X/6-31+G(d,p) level. These reactions show very low activation energies and complete endo selectivity, in agreement with the experimental data. For a dienic steroid model, the reaction presents an α-facial selectivity. Analysis of reactivity indices explains the superelectrophilic character of TADs, and low activation energy. The substituent and solvent effects are also evaluated.
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