ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 25, Number 1
JKCSEZ 25(1)
February 20, 1981 

Bromination of acetoacteanilide in non-polar medium gives the γ-brominated derivative. This unexpected result may be due to the steric hinderance during the enolization of the substrate. The structure of γ-bromoacetoacetanilide can be assigned on the basis of its 1H NMR spectrum. Additional evidence is provided by making derivatives, whick proceed without skeletal rearrangements. Structural similarity of 2-(N-phenylcarbamoyl)methylene-1,4-oxathiane with carboxin which is used as a potent fungicide prompted our investigation of the 1,4-oxathiane synthesis. It is prepared from the reaction of γ-bromoacetoacetanilide with mercaptoethanol followed by acidic dehydration in high yield.