The Ireland–Claisen rearrangement is a chemical reaction of an allylic ester with strong base to give an γ,δ-unsaturated carboxylic acid.[1][2][3]
Several reviews have been published.[4][5][6]
Mechanism
[edit]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.
See also
[edit]References
[edit]- ^ Ireland, R. E.; Mueller, R. H. (1972). "Claisen rearrangement of allyl esters". J. Am. Chem. Soc. 94 (16): 5897. doi:10.1021/ja00771a062.
- ^ Ireland, R. E.; Mueller, R. H.; Willard, A. K. (1976). "The ester enolate Claisen rearrangement. Stereochemical control through stereoselective enolate formation". J. Am. Chem. Soc. 98 (10): 2868–2877. doi:10.1021/ja00426a033.
- ^ Miller, S. P.; Morken, J. P. (2004). "Catalytic Diastereoselective Reductive Claisen Rearrangement". Organic Letters. 60 (16): 2743–2745. doi:10.1021/ol026273b. PMID 12153224.
- ^ Ziegler, F. E. (1977). "Stereo- and regiochemistry of the Claisen rearrangement: Applications to natural products synthesis". Acc. Chem. Res. 10 (6): 1423–1452. doi:10.1021/ar50114a006.
- ^ Pereira, S.; Srebnik, M. (1993). "The Ireland–Claisen rearrangement" (PDF). Aldrichimica Acta. 26 (1): 17–29. Archived from the original (PDF) on 2014-02-19. Retrieved 2014-01-25.
- ^ Chai, Y.; Hong, S.; Lindsay, H. A.; McFarland, C.; McIntosh, M. C. (2002). "New aspects of the Ireland and related Claisen rearrangements". Tetrahedron. 58 (15): 2905–2928. doi:10.1016/S0040-4020(02)00164-3.
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