Meyer-Schuster rearrangement
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Meyer-Schuster_rearrangement".

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.

Variations

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]

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.

This chemical reaction article is a stub. You can help Wikipedia by expanding it.