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The palladium-catalyzed amination of 3-bromo-4-fluoro-acetophenone was found to predominate over both the 4-fluoro nucleophilic substitution with amines and the palladium-catalyzed α-arylation of the acetyl group.
Application of an Eschenmoser sulfide contraction to a thiolactam bearing a β-acyloxy group was complicated by a competitive β-elimination reaction. Changing the β-substituent to an alkoxy group retarded the rate of elimination such that sulfide contraction products could be obtained.
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