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

Mechanism

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Related Compounds