Amino-acids and peptides. Part IX. Some neighbouring-group amino–amide and hydroxy–amide interactions

Abstract

Base-catalysed hydrolysis studies have provided evidence of neighbouring-group amino–amide interactions in compounds with the formulae H₂N·[CH₂]_x·CO·NHMe (x= 3, 4, or 5), and in 6-aminodecane-10-lactam. Acid-catalysed hydrolysis studies have indicated that transannular hydroxy-amide interactions occur with 4-hydroxyhexane-6-lactam, 5-hydroxyoctane-8-lactam, and 6-hydroxydecane-10-lactam. The mechanisms of these reactions and the significance of such processes in peptide chemistry is discussed.