- Participation of a Neighboring Amide Group in the Hydrolytic C-OAr Cleavage of 1-Acyl-2-(2-phenoxyethyl)pyrrolidines
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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.
- Dobrzeniecka, Regina
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p. 901 - 910
(2007/10/02)
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- Compounds with Bridgehead Nitrogen. 42 - 1H NMR and Stereochemistry of Isomeric 6a-Methylperhydroindolobenzoxazines and the Position of Conformational Equilibrium in Perhydropyrrolooxazine
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The 1H NMR parameters of the NCH2O protons in the spectrum of perhydropyrrolooxazine show its existence in solution at room temperature in the O-inside cis-fused conformation, rel-(3aS,6aS,6bR,10aS,11aS)6a-Methylperhydroindolobenzoxazine and rel-(3aS,6aS,6bS,10aR,11aS)-6a-methylperhydroindolobenzoxazine are shohn to adopt cis- and trans-fused conformations, respectively, for the corresponding bicyclic moiety.
- Crabb, Trevor A.,Newton, Roger F.,Rouse, Janet
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p. 113 - 116
(2007/10/02)
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