
%0 Journal Article
%A Beckwith, ALJ 
%A Goodrich, JE 
%T Free-radical rearrangement of N-chloro-amides: A synthesis of lactones
%J Australian Journal of Chemistry
%D 1965/05/01
%V 18
%N 5
%P 747-757
%K 
%R https://doi.org/10.1071/CH9650747
%U https://www.publish.csiro.au/paper/CH9650747 
%X Ultraviolet irradiation of N-chlorohexanamide with subsequent hydrolysis of the crude product affords the lactones of 4- and 5-hydroxyhexanoic acids in yields of 49% and 15% respectively. Similar results were obtained using a variety of N-chloro-amides, which were conveniently prepared in high yield by the bromine-catalysed reaction of primary amides with t-butyl hypochlorite. It is suggested that the reaction proceeds by a free-radical chain mechanism involving intramolecular hydrogen-atom transfer in amide radicals formed by dissociation of the N-Cl bond.   A similar transformation of N-chloro-amides may be induced by their treatment with cuprous chloride in carbon tetrachloride. 
