Tetrahedron

Participation of neighbouring amide group in the competitive acid catalysed hydrolysis of ether linkage and an intramolecular SN 2 reactions. 2

A Arcelli, M Papa, G Porzi, S Sandri

Index: Arcelli, Antonio; Papa, Matteo; Porzi, Gianni; Sandri, Sergio Tetrahedron, 1997 , vol. 53, # 30 p. 10513 - 10516

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Citation Number: 10

Abstract

The substrate 1 was submitted to acid hydrolysis and two reaction products (2, 3) were obtained in competitive reactions (a parallel pathway). The experimental data, elaborated by using the expressions for the parallel first-order reactions, showed the formation of 3 (an intramolecular cyclization) about three-fold slower than 2 (the previously observed hydrolytic cleavage of ether linkage). Both the reactions appear to be assisted by the protonated ...