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Ireland–Claisen rearrangement

Chemical reaction

The Ireland–Claisen rearrangement is a chemical reaction of an allylic ester with strong base to give an γ,δ-unsaturated carboxylic acid.

Several reviews have been published.

Mechanism

The Ireland–Claisen rearrangement is a type of Claisen rearrangement. The mechanism is therefore a concerted [3,3]-sigmatropic rearrangement which according to the Woodward–Hoffmann rules show a concerted, suprafacial, pericyclic reaction pathway.

References

(1972). "Claisen rearrangement of allyl esters". [[J. Am. Chem. Soc.]].
(1976). "The ester enolate Claisen rearrangement. Stereochemical control through stereoselective enolate formation". J. Am. Chem. Soc..
(2004). "Catalytic Diastereoselective Reductive Claisen Rearrangement". [[Organic Letters]].
Ziegler, F. E.. (1977). "Stereo- and regiochemistry of the Claisen rearrangement: Applications to natural products synthesis". [[Acc. Chem. Res.]].
(1993). "The Ireland–Claisen rearrangement". [[Aldrichimica Acta]].
(2002). "New aspects of the Ireland and related Claisen rearrangements". [[Tetrahedron (journal).

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