Tetrahedron p. 9729 - 9736 (1995)
Update date:2022-08-17
Topics:
Arcelli, Antonio
Porzi, Gianni
Sandri, Sergio
Evidence for the acid catalyzed hydrolysis or methyl ether linkage assisted by the neighboring amide function was obtained. The hydrolysis rate of 1 to 3 was measured at least 1.7 x 103 fold higher than that of the reference compound 5. The values of thermodynamic parameters suggest that the participation of neighboring amide group in 1 is accompanied by a lower activation enthalphy with respect to the unassisted reaction in 5. Experimental evidence, such as the kinetic isotope ratio, the positive Φ value of Bunnett-Olsen equation and ΔS++ value suggests an A2 mechanism.
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