Meyer-Schuster rearrangement
- 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.Ref|Meyer1922Ref|Swaminathan1971Ref|Vartanyan1967
Acid catalysts can include acetic acid, sulfuric acid, and hydrochloric acid. Edens "et al." have investigated the reaction mechanism.Ref|Edens1977
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.Ref|Rupe1926
References
# Meyer, K. H.; Schuster, K. "Ber." 1922, "55", 819.
# Swaminathan, S.; Narayan, K. V. "Chem. Rev." 1971, "71", 429. ( [http://dx.doi.org/10.1021/cr60273a001 Review] )
# Vartanyan, S. A.; Banbanyan, S. O. "Russ. Chem. Rev." 1967, "36", 670. (Review)
# Edens, M.; Boerner, D.; Chase, C. R.; Nass, D.; Schiavelli, M. D. "J. Org. Chem." 1977, "42", 3403-3408. (DOI|10.1021/jo00441a017)
# Rupe, H.; Kambli, E. "Helv. Chim. Acta" 1926, "9", 672.
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