Australian Journal of Chemistry

Free-radical rearrangement of N-chloro-amides: a synthesis of lactones

ALJ Beckwith, JE Goodrich

Index: Beckwith,A.L.J.; Goodrich,J.E. Australian Journal of Chemistry, 1965 , vol. 18, p. 747 - 757

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Citation Number: 35

Abstract

Abstract 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- ...

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