Meyers-Schuster重排反应

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α-炔基仲醇或叔醇经1,3-迁移异构为α,β-不饱和羰基化合物。端基炔基导致醛,链间炔基导致酮。参见Rupe重排反应



反应机理



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参考文献


1. Meyer, K. H.; Schuster, K. Ber.1922, 55, 819–823.

2. Swaminathan, S.; Narayanan,K. V. Chem. Rev1971, 71, 429–438. (Review).

3. Edens, M.; Boerner, D.;Chase, C. R.; Nass, D.; Schiavelli, M. D. J. Org. Chem1977,

42, 3403–3408.

4. Andres, J.; Cardenas, R.;Silla, E.; Tapia, O. J. Am. Chem. Soc1988, 110, 666–674.

5. Tapia, O.; Lluch, J. M.;Cardenas, R.; Andres, J. J. Am. Chem. Soc1989, 111, 829–

835.

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.

7. Yoshimatsu, M.; Naito, M.;Kawahigashi, M.; Shimizu, H.; Kataoka, T. J. Org. Chem.

1995, 60, 4798–4802.

8. Crich, D.; Natarajan, S.;Crich, J. Z. Tetrahedron 1997, 53, 7139–7158.

9. Williams, C. M.; Heim, R.;Bernhardt, P. V. Tetrahedron 2005, 61, 3771–3779.

10. Mullins, R. J.; Collins, N.R. Meyer–Schuster Rearrangement. In Name Reactions for

Homologations-PartII; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2009, pp 305


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