DOI QR코드

DOI QR Code

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


초록

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

키워드

참고문헌

  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.

피인용 문헌

  1. Photochemical Reductions of Benzil and Benzoin in the Presence of Triethylamine and TiO? Photocatalyst vol.23, pp.9, 2002, https://doi.org/10.5012/bkcs.2002.23.9.1229
  2. ChemInform Abstract: Photochemical Reduction of 1,2-Diketones in the Presence of TiO2. vol.33, pp.28, 2001, https://doi.org/10.1002/chin.200228066
  3. Photocatalysis: a promising route for 21st century organic chemistry vol.2007, pp.33, 2007, https://doi.org/10.1039/b700395c
  4. Adsorptive and Kinetic Properties on Photocatalytic Hydrogenation of Aromatic Ketones upon UV Irradiated Polycrystalline Titanium Dioxide: Differences between Acetophenone and Its Trifluoromethylated vol.116, pp.33, 2012, https://doi.org/10.1021/jp3056174
  5. Photocatalytic reduction of benzonitrile to benzylamine in aqueous suspensions of palladium-loaded titanium(IV) oxide vol.49, pp.93, 2001, https://doi.org/10.1039/c3cc46439c
  6. Photocatalytic hydrogenation of alkenes to alkanes in alcoholic suspensions of palladium-loaded titanium(IV) oxide without the use of hydrogen gas vol.4, pp.38, 2014, https://doi.org/10.1039/c4ra02275k
  7. Photochemical reactions of 1,2-diketones with silyl enol ethers vol.41, pp.1, 2015, https://doi.org/10.1007/s11164-013-1203-3
  8. Photocatalysis with TiO2 Applied to Organic Synthesis vol.68, pp.11, 2001, https://doi.org/10.1071/ch15322
  9. Organically modified titania having a metal catalyst: a new type of liquid-phase hydrogen-transfer photocatalyst working under visible light irradiation and H2-free conditions vol.18, pp.24, 2001, https://doi.org/10.1039/c6cp01847e
  10. Titanium(iv) oxide having a copper co-catalyst: a new type of semihydrogenation photocatalyst working efficiently at an elevated temperature under hydrogen-free and poison-free conditions vol.20, pp.29, 2001, https://doi.org/10.1039/c8cp02316f
  11. Photocatalytic single electron transfer reactions on TiO2 semiconductor vol.62, pp.11, 2019, https://doi.org/10.1007/s11426-019-9626-9