Meyer-Schuster rearrangement

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The Meyer-Schuster rearrangement is the chemical reaction described as an acid-catalyzed rearrangement of propargyl alcohols to α,β-unsaturated ketones.^[1][2][3]

Acid catalysts can include acetic acid, sulfuric acid, and hydrochloric acid. Edens et al. have investigated the reaction mechanism.^[4]

When catalyzed by base, the reaction is called the Favorskii reaction.

[edit] Variations

[edit] Rupe rearrangement

The reaction of tertiary alcohols containing terminal acetylenic groups does not produce the expected aldehydes, but rather α,β-unsaturated methyl ketones.^[5]

[edit] References

1. ^  Meyer, K. H.; Schuster, K. Ber. 1922, 55, 819.
2. ^  Swaminathan, S.; Narayan, K. V. Chem. Rev. 1971, 71, 429. (Review)
3. ^  Vartanyan, S. A.; Banbanyan, S. O. Russ. Chem. Rev. 1967, 36, 670. (Review)
4. ^  Edens, M.; Boerner, D.; Chase, C. R.; Nass, D.; Schiavelli, M. D. J. Org. Chem. 1977, 42, 3403-3408. (doi:10.1021/jo00441a017)
5. ^  Rupe, H.; Kambli, E. Helv. Chim. Acta 1926, 9, 672.