:Ireland–Claisen rearrangement

{{Short description|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.{{cite journal|author1=Ireland, R. E. |author2=Mueller, R. H. |journal=J. Am. Chem. Soc. |doi=10.1021/ja00771a062|title=Claisen rearrangement of allyl esters|year=1972|volume=94|issue=16|pages=5897}}{{cite journal|author1=Ireland, R. E. |author2=Mueller, R. H. |author3=Willard, A. K. |journal=J. Am. Chem. Soc.|year=1976|volume=98|pages= 2868–2877|doi=10.1021/ja00426a033|title=The ester enolate Claisen rearrangement. Stereochemical control through stereoselective enolate formation|issue=10}}{{cite journal|title=Catalytic Diastereoselective Reductive Claisen Rearrangement|author1=Miller, S. P. |author2=Morken, J. P.|doi=10.1021/ol026273b |journal=Organic Letters|year=2004|volume=60|pages= 2743–2745|issue=16|pmid=12153224}}

File:Ireland-Claisen Rearrangement Scheme.png

Several reviews have been published.{{cite journal|author=Ziegler, F. E. |journal=Acc. Chem. Res.|year=1977|volume=10|pages= 1423–1452|doi=10.1021/ar50114a006|title=Stereo- and regiochemistry of the Claisen rearrangement: Applications to natural products synthesis|issue=6}}{{cite journal|author1=Pereira, S.|author2=Srebnik, M.|journal=Aldrichimica Acta|year=1993|volume=26|issue=1|pages=17–29|url=http://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Aldrich/Acta/al_acta_26_01.pdf|title=The Ireland–Claisen rearrangement|access-date=2014-01-25|archive-date=2014-02-19|archive-url=https://web.archive.org/web/20140219094411/http://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Aldrich/Acta/al_acta_26_01.pdf|url-status=dead}}{{cite journal|author1=Chai, Y. |author2=Hong, S. |author3=Lindsay, H. A. |author4=McFarland, C. |author5=McIntosh, M. C. |journal=Tetrahedron|year=2002|volume=58|pages= 2905–2928|doi=10.1016/S0040-4020(02)00164-3|title=New aspects of the Ireland and related Claisen rearrangements|issue=15}}