Interconversion and decomposition of furanones

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Zhi Ping Xu, Chup Yew Mok, Wee Shong Chin, Hsing Hua Huang, Sheng Li and Wei Huang


Abstract

The interconversion and decomposition of furan-2(3H[hair space])- and -2(5H[hair space])-one and their methylated derivatives were studied by following the changes in their photoelectron spectra during pyrolysis. Interconversion occurred at 300–400 °C and decomposition at around 600 °C giving CO and acrolein as the only products for the unsubstituted furanones. The experimental results suggest that decarbonylation takes place through the 2(3H[hair space]) form as the common precursor.


References

  1. C. D. Hurd and F. H. Blunck, J. Am. Chem. Soc., 1938, 60, 2419 CrossRef CAS.
  2. W. J. Bailey and C. N. Bird, J. Org. Chem., 1977, 40, 3895 CrossRef.
  3. R. Taylor, The Chemistry of Functional Groups, Supplement B. The Chemistry of Derivatives, Part 2, ed. S. Patai, Wiley, Chichester, 1979 Search PubMed.
  4. H. M. Frey and I. M. Pidgeon, J. Chem. Soc., Faraday Trans. 1, 1985, 81, 1087 RSC.
  5. A. Rai-Chaudhuri, W. S. Chin, D. Kaur, C. Y. Mok and H. H. Huang, J. Chem. Soc., Perkin Trans. 2, 1993, 1249 RSC.
  6. A. Rai-Chaudhuri, W. S. Chin, C. Y. Mok and H. H. Huang, J. Chem. Res. (S), 1994, 378 Search PubMed.
  7. W. S. Chin, C. Y. Mok, H. H. Huang and H. S. Rzepa, J. Chem. Soc., Perkin Trans. 2, 1995, 427 RSC.
  8. W. Skorianetz and G. Ohloff, Helv. Chim. Acta, 1975, 58, 1272 CAS.
  9. J. A. H. Näsman and K. G. Pensar, Synthesis, 1985, 8, 786 CrossRef.
  10. Z. P. Xu, C. Y. Mok, W. S. Chin, H. H. Huang, W. Huang, H. Mutoh and S. Masuda, J. Electron Spectrosc. Relat. Phenom., 1998, 94, 1 CrossRef CAS.
  11. D. X. Wang, D. Wang, S. Li and Y. Li, J. Electron Spectrosc. Relat. Phenom., 1994, 70, 167 CrossRef CAS.
  12. K. Kimura, S. Katsumata, Y. Achiba, T. Tamazaki and S. Iwata, Handbook of HeI Photoelectron Spectra of Fundamental Organic Molecules, Japan Scientific Societies Press, Tokyo, 1981 Search PubMed.
  13. W. Tam, D. Yee and C. Brion, J. Electron Spectrosc. Relat. Phenom., 1974, 4, 77 CrossRef CAS.
  14. P. Masclet and G. Mouvier, J. Electron Spectrosc. Relat. Phenom., 1978, 14, 77 CrossRef CAS.
  15. J. P. Wineburg, C. Abrums and D. Swern, J. Heterocycl. Chem., 1975, 12, 749 CAS.
  16. B. Cederlund, Å. Jesperson and A.-B. Hörnfeldt, Acta Chem. Scand., 1971, 25, 3656 CAS.
  17. E. Guntrum, W. Kuhn, W. Spönlein and V. Jäger, Synthesis, 1986, 11, 921 CrossRef.
  18. D. X. Wang, S. Li, D. Wang and Y. Li, J. Electron Spectrosc. Relat. Phenom., 1994, 70, 173 CrossRef CAS.
  19. O. Thorstad, K. Undheim, B. Cederlund and A.-B. Hörnfeldt, Acta Chem. Scand., 1975, B29, 647 Search PubMed.
  20. J. Cossy, P.-A. Carrupt and P. Vogel, in The Chemistry of Functional Groups. Supplement A: The Chemistry of Double-bonded Functional Groups, vol. 2, ed. S. Patai, John Wiley and Sons, New York, 1989 Search PubMed.
  21. P. S. Engel, Chem. Rev., 1980, 80, 99 CrossRef CAS.
  22. J. E. Baldwin, Can. J. Chem., 1966, 44, 2051 CAS.
  23. W. R. Dolbier, Jr. and H. M. Frey, J. Chem. Soc., Perkin Trans. 2, 1974, 1674 RSC.
  24. C. J. S. M. Simpson, J. Price, G. Holmes, W. Adam, H.-D. Martin and S. Bish, J. Am. Chem. Soc., 1990, 112, 5089 CrossRef CAS.
  25. P. C. Martino and P. B. Shevlin, J. Am. Chem. Soc., 1980, 102, 5430 CrossRef CAS.
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