Ireland-Claisen rearrangement
- Ireland-Claisen rearrangement
The Ireland-Claisen rearrangement is a chemical reaction of an allylic ester with strong base to give an γ,δ-unsaturated carboxylic acid. [Ireland, R. E.; Mueller, R. H.; "J. Am. Chem. Soc." 1972, "94", 5897-5898. (DOI|10.1021/ja00771a062)] [Ireland, R. E.; Willard, A. K.; "Tetrahedron Lett." 1975, "16", 3975-3978.] [Ireland, R. E.; Mueller, R. H.; Willard, A. K.; "J. Am. Chem. Soc." 1976, "98", 2868-2877. (doi|10.1021/ja00426a033)] ["Catalytic Diastereoselective Reductive Claisen Rearrangement" S. P. Miller, J. P. Morken, "Org. Lett." 2004, "60", 2743-2745.]
Several reviews have been published. [Ziegler, F. E. "Acc. Chem. Res." 1977, "10", 1423-1452. (Review)] [Pereira, S.; Srebnik, M. "Aldrichimica Acta" 1993, "26(1)", 17-29. ( [http://www.sigmaaldrich.com/aldrich/acta/al_acta_26_01.pdf Review] )] [Chai, Y.; Hong, S.; Lindsay, H. A.; McFarland, C.; McIntosh, M. C. "Tetrahedron" 2002, "58", 2905-2928. (Review)]
Mechanism
The Ireland-Claisen rearrangement is a type of Claisen rearrangement. The mechanism is therefore a concerted [sigmatropic rearrangement| [3,3] -sigmatropic rearrangement] which according to the Woodward-Hoffmann rules show a concerted, suprafacial, pericyclic reaction pathway.
References
ee also
*Cope rearrangement
*Overman rearrangement
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