
TY  - JOUR
A1  - Beckwith, ALJ 
A1  - Goodrich, JE 
T1  - Free-radical rearrangement of N-chloro-amides: A synthesis of lactones
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1965
VL  - 18
IS  - 5
SP  - 747
EP  - 757
KW  - 
UR  - https://doi.org/10.1071/CH9650747 
N2  - 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. 
ER  -

