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Photochemical Reduction of 1,2-Diketones in the Presence of $TiO_2$


Abstract

1,2-Diketones, camphorquinone and 1-phenyl-1,2-propanedione, are converted to the corresponding $\alpha-hydroxyketones$ in moderate to good yields by TiO2-catalyzed photochemical reactions in deoxygenated alcoholic media. The reduction yield for 1-phenyl-1,2-propanedione is considerably increased by addition of water or triethylamine

Keywords

References

  1. Energy Resources through Photochemistry and Photocatalysis Gratzel, M.(ed.)
  2. Chem. Rev. v.95 Hoffmann, M. R.;Martin, S. T.;Choi, W.;Bahnemann, D. W.
  3. Chem. Rev. v.93 Fox, M. A:Dulay, M. T.
  4. In Organic Photochemistry Li, Y.;Ramamurthy, V.(eds.);Schanze, K. S.(eds.)
  5. J. Phys. Chem. v.91 Cuendet, P.;Gratzel, M.
  6. J. Org. Chem. v.58 Mahdavi, F.;Bruton, T. C.;Li, Y.
  7. Tetrahedron Lett. v.36 Park, K. H.;Joo, H. S.;Ahn, K. I.;Jun, K.
  8. J. Photochem. Photobiol. A: Chem. v.107 Brezova, V.;Blazkova, A.;Havlinova, S. B.
  9. Langmuir v.14 Ferry, J. L.;Glaze, W. H.
  10. Heterocylces v.53 Pace, A.;Buscemi, S.;Vivona, N.;Caronna, T.
  11. Langmuir v.15 Tada, H.;Teranishi, K.;Ito. S.
  12. J. Org. Chem. v.57 Joyce-Pruden, C.;Pross, J. K.;Li, Y.
  13. Macromol. Chem. Phys. v.200 Nie, J.;Andrzejewska, E.;Rabek, J. F.;Linden, L. A.;Fouassier, J. P.;Paczkowski, J.;Scigalski, F.;Wrzyszczynski, A.
  14. Polymer v.41 Sun, G. J.;Chae, K. H.
  15. Tetrahedron v.52 Adam, W.;Korb, M. N.
  16. Chem. Commun. Rozen, S.;Bareket, Y.
  17. Tetrahedron Lett. v.55 Dayan, S.;Bareket, Y.;Rozen, S.
  18. Chem. Lett. Chenevert, R.;Thiboutot, S.
  19. Tetrahedron: Asymmetry v.7 Nakamura, K.;Kondo, S-I.;Kawai, Y.;Hida, K.;Kitano, K.;Ohno, A.
  20. Bull. Chem. Soc. Jpn. v.72 Kawai, Y.;Hida, K.;Tsujimoto, M.;Kondo, S.-I.;Kitano, K.;Nakamura, K.;Ohno, A.
  21. Chem. Pharm. Bull. v.37 Takeshita, M.;Sato, T.
  22. J. Org. Chem. v.55 Hata, H.;shimizu, S.;Hattori, S.;Yamada, H.
  23. J. Chem. Soc., Perkin Trans. 1 Fumio, T.;Koichi, T.;Tange, H.
  24. J. Org. Chem. v.55 Zoeller, J. R;Ackerman, C. J.
  25. J. Org. Chem. v.54 Angelo, C.;Ombretta, P.
  26. Tetrahedron Lett. v.41 Hayakawa, R.;Sahara, T.;Shimizu, M.
  27. Acta Chem. Scand v.24 Thoren, S.
  28. J. Am. Chem. Soc. v.90 Monroe, B. M.;Weiner, S. A.;Hammond, G. S.
  29. Advanced Organic Chemistry, Part A, 4th Ed. Carey, F. A.;Sundberg, R. J.
  30. Tetrahedron Lett v.21 Kanno, T.;Oguchi, T.;Sakuragi, H.;Tokumaru, T.

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