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Claisen Rearrangement
Claisen rearrangement is one of [3,3]-sigmatropic rearrangements which provides γ,δ-unsaturated carbonyl compounds from ally vinyl ethers and allyl phenols. The reaction is considered to proceed via chair-like transition state and has an advantage that it is expected from substrate’s stereochemistry. Modified Claisen rearrangement reactions such as aza-Claisen, Johnson-Claisen, Eschenmoser-Claisen and Ireland-Claisen rearrangement are used according to the choice and property of substrates and products.
- Reagents:
- Allyl vinyl ethers, Allyl phenyl ethers
- Reactants:
- Lewis acids
- Products:
- γ,δ-Unsaturated aldehydes, o-Allylphenols
- Scheme:
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- Original literature:
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- Über Umlagerung von Phenol-allyläthern in C-Allyl-phenole
- Review literature:
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- Claisen Rearrangement over the Past Nine Decades
