Name Reactions pp 353-354 | Cite as

Meyer–Schuster rearrangement


The isomerization of secondary and tertiary α-acetylenic alcohols to α,β- unsaturated carbonyl compounds via1,3-shift. When the acetylenic group is terminal, the products are aldehydes, whereas the internal acetylenes give ketones. Cf. Rupe rearrangement.


  1. 1.
    Meyer, K. H.; Schuster, K. Ber. 1922, 55, 819–823.Google Scholar
  2. 2.
    Swaminathan, S.; Narayanan, K. V. Chem. Rev. 1971, 71, 429–438. (Review).CrossRefGoogle Scholar
  3. 3.
    Edens, M.; Boerner, D.; Chase, C. R.; Nass, D.; Schiavelli, M. D. J. Org. Chem. 1977, 42, 3403–3408.CrossRefGoogle Scholar
  4. 4.
    Andres, J.; Cardenas, R.; Silla, E.; Tapia, O. J. Am. Chem. Soc. 1988, 110, 666–674.CrossRefGoogle Scholar
  5. 5.
    Tapia, O.; Lluch, J. M.; Cardenas, R.; Andres, J. J. Am. Chem. Soc. 1989, 111, 829–835.CrossRefGoogle Scholar
  6. 6.
    Brown, G. R.; Hollinshead, D. M.; Stokes, E. S.; Clarke, D. S.; Eakin, M. A.; Foubister, A. J.; Glossop, S. C.; Griffiths, D.; Johnson, M. C.; McTaggart, F.; Mirrlees, D. J.; Smith, G. J.; Wood, R. J. Med. Chem. 1999, 42, 1306–1311.CrossRefGoogle Scholar
  7. 7.
    Yoshimatsu, M.; Naito, M.; Kawahigashi, M.; Shimizu, H.; Kataoka, T. J. Org. Chem. 1995, 60, 4798–4802.CrossRefGoogle Scholar
  8. 8.
    Crich, D.; Natarajan, S.; Crich, J. Z. Tetrahedron 1997, 53, 7139–7158.CrossRefGoogle Scholar
  9. 9.
    Williams, C. M.; Heim, R.; Bernhardt, P. V. Tetrahedron 2005, 61, 3771–3779.CrossRefGoogle Scholar
  10. 10.
    Mullins, R. J.; Collins, N. R. Meyer–Schuster Rearrangement. In Name Reactions for Homologations-Part II; Li, J. J., Corey, E. J., Eds.; Wiley & Sons: Hoboken, NJ,2009, pp 305-318. (Review).Google Scholar

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© Springer-Verlag Berlin Heidelberg 2009

Authors and Affiliations

  1. 1.Dept. Discovery ChemistryBristol-Myers Squibb CompanyWallingfordUSA

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