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 evaluation of the relevant activation parameters. Substituent effects, as quantified by means of 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.

Frenna, V., Lo Meo, P., Palumbo Piccionello, A., Spinelli, D. (2019). Unexpected Substituent Effects in the Iso-Heterocyclic Boulton-Katritzky Rearrangement of 3-Aroylamino-5-Methyl-1,2,4-Oxadiazoles: a Mechanistic Study. JOURNAL OF PHYSICAL CHEMISTRY. A, MOLECULES, SPECTROSCOPY, KINETICS, ENVIRONMENT, & GENERAL THEORY, 123, 10004-10010 [10.1021/acs.jpca.9b08675].

Unexpected Substituent Effects in the Iso-Heterocyclic Boulton-Katritzky Rearrangement of 3-Aroylamino-5-Methyl-1,2,4-Oxadiazoles: a Mechanistic Study

Frenna, Vincenzo;Lo Meo, Paolo
;
Palumbo Piccionello, Antonio;Spinelli, Domenico
2019-01-01

Abstract

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 evaluation of the relevant activation parameters. Substituent effects, as quantified by means of 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.
Settore CHIM/06 - Chimica Organica
Frenna, V., Lo Meo, P., Palumbo Piccionello, A., Spinelli, D. (2019). Unexpected Substituent Effects in the Iso-Heterocyclic Boulton-Katritzky Rearrangement of 3-Aroylamino-5-Methyl-1,2,4-Oxadiazoles: a Mechanistic Study. JOURNAL OF PHYSICAL CHEMISTRY. A, MOLECULES, SPECTROSCOPY, KINETICS, ENVIRONMENT, & GENERAL THEORY, 123, 10004-10010 [10.1021/acs.jpca.9b08675].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/382178
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