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Pseudo-first-order rate constants have been measured spectrophotometrically for the reactions of benzyl 4-pyridyl carbonate 6 with a series of alicyclic secondary amines in at . The plots of vs. [amine] curve upward, indicating that the reactions proceed through a stepwise mechanism with two intermediates, a zwitterionic tetrahedral intermediate and its deprotonated form . This contrasts to the report that the corresponding reactions of benzyl 2-pyridyl carbonate 5 proceed through a forced concerted pathway. The values for the reactions of 6 have been dissected into the second-order rate constant and the thirdorder rate constant . The Brnsted-type plots are linear with and 1.18 for and , respectively. The for the reaction of 6 is smaller than the second-order rate constant for the corresponding reaction of 5, although 4-pyridyloxide in 6 is less basic and a better nucleofuge than 2-pyridyloxide in 5.

bulletin of the korean chemical society

Kinetics and Reaction Mechanism for Aminolysis of Benzyl 4-Pyridyl Carbonate in H<sub>2</sub>O: Effect of Modification of Nucleofuge from 2-Pyridyloxide to 4-Pyridyloxide on Reactivity and Reaction Mechanism

Kinetics and Reaction Mechanism for Aminolysis of Benzyl 4-Pyridyl Carbonate in H2O: Effect of Modification of Nucleofuge from 2-Pyridyloxide to 4-Pyridyloxide on Reactivity and Reaction Mechanism

Kinetics and Reaction Mechanism for Aminolysis of Benzyl 4-Pyridyl Carbonate in H₂O: Effect of Modification of Nucleofuge from 2-Pyridyloxide to 4-Pyridyloxide on Reactivity and Reaction Mechanism