Concerted Pyridinolysis of Aryl 2,4,6-Trinitrophenyl Carbonates

Concerted Pyridinolysis of Aryl 2,4,6-Trinitrophenyl Carbonates

The Brønsted plots for the title reactions are linear with slopes of 0.53−0.56. The magnitude of the slopes and the fact that there are no breaks at the predicted pK a for stepwise mechanisms indicate that these reactions are concerted. This finding is in great contrast to the stepwise mechanisms fo...

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Veröffentlicht in:Journal of organic chemistry 2009-08, Vol.74 (16), p.6374-6377
Hauptverfasser: Castro, Enrique A, Ramos, Mariela, Santos, José G
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Kinetics and mechanisms
Organic chemistry
Preparations and properties
Reactivity and mechanisms
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Zusammenfassung:The Brønsted plots for the title reactions are linear with slopes of 0.53−0.56. The magnitude of the slopes and the fact that there are no breaks at the predicted pK a for stepwise mechanisms indicate that these reactions are concerted. This finding is in great contrast to the stepwise mechanisms found for the pyridinolysis of other carbonates. The concerted mechanism is attributed to the fact that the title carbonates possess two O-aryl groups, one of them being an exceptionally good nucleofuge.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo901137f