Advertisement

Name Reactions pp 480-481 | Cite as

Rupe rearrangement

  • Jie Jack Li
Chapter

Acid-catalyzed rearrangement of tertiary α-acetylenic (terminal) alcohols, leading to the formation of α,β-unsaturated ketones rather than the corresponding α,βunsaturated aldehydes. Cf.Meyer–Schuster rearrangement.

Keywords

Inorganic Chemistry Organic Chemistry Unsaturated Aldehyde 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    Rupe, H.; Kambli, E. Helv. Chim. Acta 1926, 9, 672.CrossRefGoogle Scholar
  2. 2.
    Swaminathan, S.; Narayanan, K. V. Chem. Rev. 1971, 71, 429–438. (Review).CrossRefGoogle Scholar
  3. 3.
    Hasbrouck, R. W.; Anderson Kiessling, A. D. J. Org. Chem. 1973, 38, 2103–2106.CrossRefGoogle Scholar
  4. 4.
    Baran, J.; Klein, H.; Schade, C.; Will, E.; Koschinsky, R.; Bäuml, E.; Mayr, H. Tetrahedron 1988, 44,2181–2184.CrossRefGoogle Scholar
  5. 5.
    Barre, V.; Massias, F.; Uguen, D. Tetrahedron Lett. 1989, 30, 7389–7392.CrossRefGoogle Scholar
  6. 6.
    An, J.; Bagnell, L.; Cablewski, T.; Strauss, C. R.; Trainor, R. W. J. Org. Chem. 1997, 62, 2505–2511.CrossRefGoogle Scholar
  7. 7.
    Yadav, J. S.; Prahlad, V.; Muralidhar, B. Synth. Commun. 1997, 27, 3415–3418.CrossRefGoogle Scholar
  8. 8.
    Takeda, K.; Nakane, D.; Takeda, M. Org. Lett. 2000, 2, 1903–1905.CrossRefGoogle Scholar
  9. 9.
    Weinmann, H.; Harre, M.; Neh, H.; Nickisch, K.; Skötsch, C.; Tilstam, U. Org. Proc. Res. Dev. 2002, 6, 216–219.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

Copyright information

© Springer-Verlag Berlin Heidelberg 2009

Authors and Affiliations

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

Personalised recommendations