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Unusual Transformation of Cyclobutenediones into Butenolides

Cyclobutenediones 에서 Butenolides로의 이색적인 반응

  • Published : 2003.06.20

Abstract

Butenolides are prepared from cyclobutenediones when cyclobutenediones are treated with lithium trimethylsilylacetylene, and quenched with water. A plausible mechanism, which contains an allene as an intermediate, is proposed. The usual diradical intermediate may not be formed because of the bulkiness of trimethylsilyl group, and the allenic intermediate may be stabilized by the ${\alpha}$-silyl group.

Keywords

Butenolides; Cyclobutendiones; Allene

References

  1. Perri, S. T.; Foland, L. D.; Decker,O. H.; Moore, H. W. J. Org. Chem. 1986, 52, 3067.
  2. Lee, K. H.; Moore,H. W. J. Org. Chem. 1995, 60, 735 https://doi.org/10.1021/jo00108a045
  3. Lipshultz, B. H.; Pegram, J. J. Tetrahedron Lett. 1980,21, 2343.
  4. Lee, K. H., Huang, B. R, Tzeng, C. C. Bioorg. Med.Chem. Lett. 1999, 9, 241. https://doi.org/10.1016/S0960-894X(98)00727-6
  5. Foland, L. D.; Karlson, J. O.; Perri, S. T.; Schwabe,R.; Xu, S. L.; Patil, S.; Moore, H. W. J. Am. Chem. Soc.1989, 111, 975. https://doi.org/10.1021/ja00185a030
  6. Fujita, E.; Fuji, K.; Nakano, S. Synthesis 1975, 276.
  7. Liebskind,L. S.; Wang, J. Tetrahedron Lett. 1990, 31, 4293. https://doi.org/10.1016/S0040-4039(00)97604-4
  8. Liebskind, L. S.; Fengl, R. W.; Wirtz, K. R.;Shawe, T. T. J. Org. Chem. 1988, 53, 2482. https://doi.org/10.1021/jo00246a017
  9. Houk, K. N.; Rondan,N. G. J. Am. Chem. Soc. 1985, 107, 2099. https://doi.org/10.1021/ja00293a046
  10. Decker, O.; Moore,H. W. Chem. Rev. 1986, 86, 821. https://doi.org/10.1021/cr00075a006
  11. Lee, K. H.; More, H. W. Tetrahedron Lett. 1993, 34, 235. https://doi.org/10.1016/S0040-4039(00)60555-5
  12. Cohen, S,; Cohen, S. G. J. Am. Chem. Soc. 1966,1533.
  13. Czernecki, C.; Georgoulis, C.; Provelenghiou, C.Tetrahedron Lett. 1976, 3535.
  14. Liu, H.;Tomooka, C. S.; Xu, S. L.; Yerxa, B. R.; Sullivan, R.W.; Xiong, Y.; Moore, H. W. Organic Synthesis 1999,76, 189. https://doi.org/10.15227/orgsyn.076.0189
  15. Iwashiege, T.; Saeki,H. Pharm. Bull. 1967, 15, 1803. https://doi.org/10.1248/cpb.15.1803
  16. Gao, X., Nakadai, M., Snider, B. B. Org. Lett. 2003, 5,541.
  17. Perri, S. T.; Dyke, H. J.; Moore, H.W. J. Org. Chem. 1989, 54, 2032. https://doi.org/10.1021/jo00270a004
  18. Liebskind, L. S.; Baysdon, S. L. Tetrahedron Lett.1984. 25, 1747. https://doi.org/10.1016/S0040-4039(01)90031-0
  19. Houk, K. N.; Kirmse, W.; Rondan, N. G. J. Am.Chem. Soc. 1984, 106, 7989. https://doi.org/10.1021/ja00337a067
  20. Teidemann, R.; Moore,H. W. J. Am. Chem. Soc. 1998, 120, 3801. https://doi.org/10.1021/ja980039s
  21. Brown, R. C., Bataille, C. J. R., Bruton, G., Hinks, J.D., Swain, N. A. J. Org. Chem. 2001, 66, 6719. https://doi.org/10.1021/jo015829q
  22. Liebskind, L. S.; Iyer, S.; Jewell, C. F. Jr. J. Org. Chem.1986, 51, 3065. https://doi.org/10.1021/jo00365a043
  23. Verman, S. K.; Nguyen, Q. H.; McDougall,J. M.; Fleischer, E. B.; Moore, H. W. J. Org. Chem.2000, 65, 3379. https://doi.org/10.1021/jo991765w