The Eschenmoser-Claisen rearrangement uses heat to produce an γ,δ-unsaturated amide from an allylic alcohol and N,N-dimethylacetamide dimethyl acetal. First N,N-dimethylacetamide dimethyl acetal loses a methoxide ion to make an iminium ion, which is attacked by the allylic alcohol. Formation of a second iminium ion, followed by a proton abstraction, results in a 1,5-diene (ketene aminal) intermediate that undergoes a Claisen-type sigmatropic rearrangement to create the final γ,δ-unsaturated amide product.

  • Reactant: Allylic Alcohol, N,N-dimethylacetamide Dimethyl Acetal, Xylene
  • Product: γ,δ-unsaturated Amine
  • Type of Reaction: Rearrangement


Top Citations

Original Paper

Related Reactions

Related Compounds

  • N,N-dimethylacetamide dimethyl acetal (CAS 18871-66-4)
  • Allylic alcohol
By shuhan yang


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