19432-88-3Relevant articles and documents
Participation of a Neighboring Amide Group in the Hydrolytic C-OAr Cleavage of 1-Acyl-2-(2-phenoxyethyl)pyrrolidines
Dobrzeniecka, Regina
, p. 901 - 910 (2007/10/02)
Measurements are reported on the kinetics of acid-catalyzed hydrolysis of 1-acetyl- and 1-propionyl-2-(2-phenoxyethyl)pyrrolidine.The pseudo-first-order rate constants, kobs, were obtained: kobs = kA + kB, where kA and kB refer to the rate constants for the formation of 2-(2-phenoxyethyl)pyrrolidine A and 2-(2-hydroxyethyl)pyrrolidine B, respectively.Formation of the product B with consequent liberation of the phenol is attributed to the effect of neighboring amide group participation.A mechanism comprising a six-membered cyclic intermediate has been proposed for hydrolysis leading to cleavage of the ether bond.