The document discusses the Claisen rearrangement reaction, which involves the [3,3]-sigmatropic rearrangement of an allyl vinyl ether to form a γ,δ-unsaturated carbonyl. It provides examples of different types of Claisen rearrangements, including aromatic, aliphatic, thio-, tandem, aza-, retro-Claisen rearrangements. It also gives specific examples of applications for synthesizing required allyl enol ethers and mentions the Eschenmoser amide Claisen process and use in synthesizing a male dried bean beetle sex pheromone.

1. Applications of Claisen
Rearrangement
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2. What is Claisen rearrangement
 The Claisen rearrangement is a powerful carbon–carbon bond-forming chemical
reaction discovered by Rainer Ludwig Claisen. The heating of
an allyl vinyl ether will initiate a [3,3]-sigmatropic rearrangement to give a γ,δ-
unsaturated carbonyl.

3. Applications of Claisen Rearrangement
• Aromatic Claisen Rearrangement
• Aliphatic Claisen Rearrangement
• Thio-Claisen Rearrangement
• Tandem Reaction
• Aza-Claisen Rearrangement
• Thio-Claisen Rearrangement
• Retro-Claisen Rearrangement

4. Aromatic Claisen Rearrangement
The aromatic variation of the Claisen rearrangement is the [3,3]-sigmatropic rearrangement of
an allyl phenyl ether to an intermediate which quickly tautomerizes to an ortho-substituted phenol

5. Aliphatic Claisen Rearrangement
The aliphatic Claisen (oxa-Cope), in contrast to the all-carbon Cope, has the advantage that the
equilibrium constant is reliably favorable in the direction of the carbonyl compound. Claisen himself
discovered the earliest example of sigmatropic rearrangement of an allyl enol ether: Claisen Chem.
Ber. 1912, 42, 3157
several effective protocols to synthesize the required allyl enol ethers have been developed: the enol
ether Claisen, the Johnson orthoester Claisen, and the Ireland silyl ketene acetal Claisen.

6. The Eschenmoser Amide Claisen Process
Eschenmoser Helv. Chim. Acta 1964,

7. Claisen Rearrangment of a Propargyl alcohol
Male Dried Bean Beetle Sex Pheromone. Kocienski, P.; Cernogliaro, G.; Feldstein, G. J. Org.
Chem. 1977, 42, 353

8. File usage
• www.commons.wikimedia.org/wiki/File:Over
man_Rearrangement
• www.chem.wisc.edu/areas
• www.organic-chemistry.org
› Reactions › Name Reactions
• xlink.rsc.org › Journals › Organic &
Biomolecular