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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.[1][2][3][4]

Several reviews have been published.[5][6][7]

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

  1. ^ Ireland, R. E.; Mueller, R. H.; J. Am. Chem. Soc. 1972, 94, 5897-5898. (doi:10.1021/ja00771a062)
  2. ^ Ireland, R. E.; Willard, A. K.; Tetrahedron Lett. 1975, 16, 3975-3978.
  3. ^ Ireland, R. E.; Mueller, R. H.; Willard, A. K.; J. Am. Chem. Soc. 1976, 98, 2868-2877. (doi:10.1021/ja00426a033)
  4. ^ "Catalytic Diastereoselective Reductive Claisen Rearrangement" S. P. Miller, J. P. Morken, Org. Lett. 2004, 60, 2743-2745.
  5. ^ Ziegler, F. E. Acc. Chem. Res. 1977, 10, 1423-1452. (Review)
  6. ^ Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26(1), 17-29. (Review)
  7. ^ Chai, Y.; Hong, S.; Lindsay, H. A.; McFarland, C.; McIntosh, M. C. Tetrahedron 2002, 58, 2905-2928. (Review)

See also
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Ireland-Claisen_rearrangement". A list of authors is available in Wikipedia.
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