Photoinduced reductions of chalcone derivatives in the presence of amines

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 97, Issue 1-2, 1996, Pages 33-43

  Xu, Jian Hua ^a   Chen, Chuan Feng ^a   Ouyang, Xue ^a   Wei, Jing Hua ^a   Liu, You Cheng ^b  

^a NANJING UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

Amines; Chalcone derivatives; Photoinduced reduction

Indexed keywords

EID: 0030596440     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/1010-6030(96)04310-9     Document Type: Article

References (82)

1. [1] S.G. Cohn, A. Parola and G.H. Parsons, Chem. Rev., 73 (1973) 141; P.J. Wagner, Top. Curr. Chem., 66 (1976) 1; M. Hoshino and H. Shizuka, in M.A. Fox and M. Chanon (eds.), Photoinduced Electron Transfer, Elsevier, New York, 1988, Part C, Chapter 4.5, pp. 313-371.
2. [1] S.G. Cohn, A. Parola and G.H. Parsons, Chem. Rev., 73 (1973) 141; P.J. Wagner, Top. Curr. Chem., 66 (1976) 1; M. Hoshino and H. Shizuka, in M.A. Fox and M. Chanon (eds.), Photoinduced Electron Transfer, Elsevier, New York, 1988, Part C, Chapter 4.5, pp. 313-371.
3. [1] S.G. Cohn, A. Parola and G.H. Parsons, Chem. Rev., 73 (1973) 141; P.J. Wagner, Top. Curr. Chem., 66 (1976) 1; M. Hoshino and H. Shizuka, in M.A. Fox and M. Chanon (eds.), Photoinduced Electron Transfer, Elsevier, New York, 1988, Part C, Chapter 4.5, pp. 313-371.
4. [2] R.C. Cookson, J. Hudec and N.A. Mirza, J. Chem. Soc., Chem. Commun., (1968) 180.
5. [3] (a) N.J. Pienta and J.E. Mckimmey, J. Am. Chem. Soc., 104 (1982) 5501;
6. (b) D.W. Smith and N.J. Pienta, Tetrahedron Lett., (1984) 915.
7. [4] (a) U.C. Yoon and P.S. Mariano, Acc. Chem. Res., 25 (1992) 233;
8. (b) D.I. Schuster, in S. Patai and Z. Rapoport (eds.), The Chemistry of Enones, Wiley, Chichester, West Sussex, 1989, pp. 623-756;
9. (c) N.J. Pienta, in M.A. Fox and M. Chanon (eds.), Photoinduced Electron Transfer, Elsevier, New York, 1988, Part C, Chapter 4.7, pp. 421-486.
10. [5] (a) D.I. Schuster and A.M. Insogna, J Org. Chem., 56 (1991) 1879;
11. (b) Y.T. Jeon, C.P. Lee and P.S. Mariano, J. Am. Chem. Soc., 113 (1991) 8847; W. Xu, X.M. Zhang and P.S. Mariano, J. Am. Chem. Soc., 113 (1991) 8863;
12. (b) Y.T. Jeon, C.P. Lee and P.S. Mariano, J. Am. Chem. Soc., 113 (1991) 8847; W. Xu, X.M. Zhang and P.S. Mariano, J. Am. Chem. Soc., 113 (1991) 8863;
13. (c) R.S. Givens, R. Singh, J.Y. Xu and Y.H. Park, Tetrahedron Lett., (1990) 6793;
14. (d) J. Mattey, A. Banning, E.W. Bischof, A. Heildbreder and J. Runsink, Chem. Ber., 125 (1992) 2119.
15. [6] (a) C. Harries and F. Hübner, Ann., 296 (1897) 295; A. Russel, J. Todd and C. Wilson, J. Chem. Soc., (1934) 1940; L.R. Finch and D.E. White, J. Chem. Soc., ( 1950) 3367;
16. [6] (a) C. Harries and F. Hübner, Ann., 296 (1897) 295; A. Russel, J. Todd and C. Wilson, J. Chem. Soc., (1934) 1940; L.R. Finch and D.E. White, J. Chem. Soc., ( 1950) 3367;
17. [6] (a) C. Harries and F. Hübner, Ann., 296 (1897) 295; A. Russel, J. Todd and C. Wilson, J. Chem. Soc., (1934) 1940; L.R. Finch and D.E. White, J. Chem. Soc., ( 1950) 3367;
18. (b) M. Gaweda, B. Kawalek, L. Lebioda, J. Mirek and M. Ciechanowicz-Rutkowska, Pol. J. Chem., 52 (1978) 1747.
19. [7] (a) B. Pandey, R.K. Tikare, M. Muneer, P.V. Kamat and M.V. George, Chem. Ber., 119 (1986) 917;
20. (b) E.L. Totton, R.T. Bass, Jr., F.N. Kiruti and B. Twitty, J. Org. Chem., 46 (1981) 3547.
21. [8] J.B. Conant and H.B. Cutter, J. Am. Chem. Soc., 48 (1926) 1016.
22. [9] M. Morioka, Y. Takeuchi, H. Mizuno and M. Suzuki, Nippon Kagaku Kaishi, (1980) 1300; Chem. Abstr., (1980) 94-65262.
23. [9] M. Morioka, Y. Takeuchi, H. Mizuno and M. Suzuki, Nippon Kagaku Kaishi, (1980) 1300; Chem. Abstr., (1980) 94-65262.
24. [10] H. Stamm, A. Sommer, A. Onistschenko and A. Woderer, J. Org. Chem., 51 (1986) 4979.
25. [11] (a) K. Takaki, F. Beppu, S. Tanaka, Y. Tsubaki, T. Jintoku and Y. Fujiwara, J. Chem. Soc., Chem. Commun., (1990) 516; K. Takaki, K. Nagase, F. Beppu and Y. Fujiwara, Chem. Lett., (1991) 1665;
26. [11] (a) K. Takaki, F. Beppu, S. Tanaka, Y. Tsubaki, T. Jintoku and Y. Fujiwara, J. Chem. Soc., Chem. Commun., (1990) 516; K. Takaki, K. Nagase, F. Beppu and Y. Fujiwara, Chem. Lett., (1991) 1665;
27. (b) K. Takaki, F. Beppu, I. Nakagawa and Y. Fujiwara, Chem. Lett., (1992) 535.
28. [12] A.Z. Rubezhov, Tetrahedron Lett., 25 (1977) 2189.
29. [13] (a) R. Pasternak, Helv. Chim. Acta, 31 (1948) 753; I.A. Korshunov and Yu. V. Vodzinskiy, Zh. Fiz. Khim., 27 (1953) 1152; P.J. Simonet and A. Albisson, Bull. Soc. Chim. Fr., (1971) 1125;
30. [13] (a) R. Pasternak, Helv. Chim. Acta, 31 (1948) 753; I.A. Korshunov and Yu. V. Vodzinskiy, Zh. Fiz. Khim., 27 (1953) 1152; P.J. Simonet and A. Albisson, Bull. Soc. Chim. Fr., (1971) 1125;
31. [13] (a) R. Pasternak, Helv. Chim. Acta, 31 (1948) 753; I.A. Korshunov and Yu. V. Vodzinskiy, Zh. Fiz. Khim., 27 (1953) 1152; P.J. Simonet and A. Albisson, Bull. Soc. Chim. Fr., (1971) 1125;
32. (b) F. Fournier, J. Berthelot and J.-J. Basselier, Tetrahedron, 41 (1985) 5667.
33. [14] A. Hinig, Chem. Ber., 11 (1952) 1056.
34. [15] A.T. Nielson and W.J. Haulihan, Org. Reactions, 16 (1968) 44.
35. [16] (a) M. Okubo, Bull. Chem. Soc. Jpn., 50 (1977) 2379.
36. (b) J. Harboar and A.V. Guzzo, Mol. Phys., 20 (1971) 565; 23 (1973) 151.
37. (b) J. Harboar and A.V. Guzzo, Mol. Phys., 20 (1971) 565; 23 (1973) 151.
38. [17] (a) Z. Dinya, S. Kiss, J. Balint and R. Bognar, Stud. Org. Chem., 23 (1986) 93-101.
39. (b) V.G. Mitina, B.A. Zadorozhnyi and V.F. Lavrushin, Zh. Obshch. Khim., 45 (1975) 2713; V.G. Mitina, M. Reinhardt and V.F. Lavrushin, Zh. Obshch. Khim., 50 (1980) 134; M. Reinhardt, A.A. Sukhorukov, A. Raushal and V.F. Lavrushin, Khim. Geterotsikl. Soedin., (1977) 1202.
40. (b) V.G. Mitina, B.A. Zadorozhnyi and V.F. Lavrushin, Zh. Obshch. Khim., 45 (1975) 2713; V.G. Mitina, M. Reinhardt and V.F. Lavrushin, Zh. Obshch. Khim., 50 (1980) 134; M. Reinhardt, A.A. Sukhorukov, A. Raushal and V.F. Lavrushin, Khim. Geterotsikl. Soedin., (1977) 1202.
41. (b) V.G. Mitina, B.A. Zadorozhnyi and V.F. Lavrushin, Zh. Obshch. Khim., 45 (1975) 2713; V.G. Mitina, M. Reinhardt and V.F. Lavrushin, Zh. Obshch. Khim., 50 (1980) 134; M. Reinhardt, A.A. Sukhorukov, A. Raushal and V.F. Lavrushin, Khim. Geterotsikl. Soedin., (1977) 1202.
42. (c) G. Montaudo and S. Caccamese, J. Org. Chem., 38 (1973) 710; S. Caccamese, J.A. McMillan and G. Montaudo, J. Org. Chem., 43 (1978) 2703.
43. (c) G. Montaudo and S. Caccamese, J. Org. Chem., 38 (1973) 710; S. Caccamese, J.A. McMillan and G. Montaudo, J. Org. Chem., 43 (1978) 2703.
44. [18] S.W. Baldwin, Org. Photochem., 5 (1981) 123; P.J. Wagner and D.J. Bucheck, J. Am. Chem. Soc., 91 (1969) 5090.
45. [18] S.W. Baldwin, Org. Photochem., 5 (1981) 123; P.J. Wagner and D.J. Bucheck, J. Am. Chem. Soc., 91 (1969) 5090.
46. [19] H. Miyasaka, K. Morila, M. Kiri and N. Mataga, Ultrafast Phenomenon, Vol. VII, Springer, Berlin, 1990, p. 498; H. Miyasaka, K. Monta, K. Kamada and N. Malaga, Bull. Chem. Soc. Jpn., 63 ( 1990) 3385; H. Miyasaka, M. Morita, K. Kamada, K. Kiri, T. Nagata and N. Mataga, Bull. Chem. Soc. Jpn., 64 (1991) 3229; H. Miyasaka, T. Nagata, M. Kiri and N. Mataga, J. Phys. Chem., 96 (1992) 8060.
47. [19] H. Miyasaka, K. Morila, M. Kiri and N. Mataga, Ultrafast Phenomenon, Vol. VII, Springer, Berlin, 1990, p. 498; H. Miyasaka, K. Monta, K. Kamada and N. Malaga, Bull. Chem. Soc. Jpn., 63 ( 1990) 3385; H. Miyasaka, M. Morita, K. Kamada, K. Kiri, T. Nagata and N. Mataga, Bull. Chem. Soc. Jpn., 64 (1991) 3229; H. Miyasaka, T. Nagata, M. Kiri and N. Mataga, J. Phys. Chem., 96 (1992) 8060.
48. [19] H. Miyasaka, K. Morila, M. Kiri and N. Mataga, Ultrafast Phenomenon, Vol. VII, Springer, Berlin, 1990, p. 498; H. Miyasaka, K. Monta, K. Kamada and N. Malaga, Bull. Chem. Soc. Jpn., 63 ( 1990) 3385; H. Miyasaka, M. Morita, K. Kamada, K. Kiri, T. Nagata and N. Mataga, Bull. Chem. Soc. Jpn., 64 (1991) 3229; H. Miyasaka, T. Nagata, M. Kiri and N. Mataga, J. Phys. Chem., 96 (1992) 8060.
49. [19] H. Miyasaka, K. Morila, M. Kiri and N. Mataga, Ultrafast Phenomenon, Vol. VII, Springer, Berlin, 1990, p. 498; H. Miyasaka, K. Monta, K. Kamada and N. Malaga, Bull. Chem. Soc. Jpn., 63 ( 1990) 3385; H. Miyasaka, M. Morita, K. Kamada, K. Kiri, T. Nagata and N. Mataga, Bull. Chem. Soc. Jpn., 64 (1991) 3229; H. Miyasaka, T. Nagata, M. Kiri and N. Mataga, J. Phys. Chem., 96 (1992) 8060.
50. [20] K.S. Peters and J. Lee, J. Phys. Chem., 97 (1993) 3761.
51. [21] D.I. Schuster, I.M. Nunez and C.B. Chan, Tetrahedron Lett., (1981) 1187.
52. [22] R. Bonneau, J. Am. Chem. Soc., 102 (1980) 3816; D.I. Schuster, R. Bonneau, D.A. Dunn, J.M. Rao and J. Joussot-Dubien, J. Am. Chem. Soc., 106 (1984) 2706; D.A. Dunn, D.I. Schuster and R. Bonneau, J. Am. Chem. Soc., 107 (1985) 2802; D. Weir, J.C. Scaiano and D.I. Schuster, Can. J. Chem., 66 (1988) 2595; D.I. Schuster, G.E. Heibel, P.B. Brown, N.J. Turro and C.V. Kumar, J. Am. Chem. Soc., 110 (1988) 8261; D.I. Schuster, D.A. Dunn, G.E. Heibel, P.B. Brown, J.M. Rao, J. Woning and R. Bonneau, J. Am. Chem. Soc., 113 (1991) 6245.
53. [22] R. Bonneau, J. Am. Chem. Soc., 102 (1980) 3816; D.I. Schuster, R. Bonneau, D.A. Dunn, J.M. Rao and J. Joussot-Dubien, J. Am. Chem. Soc., 106 (1984) 2706; D.A. Dunn, D.I. Schuster and R. Bonneau, J. Am. Chem. Soc., 107 (1985) 2802; D. Weir, J.C. Scaiano and D.I. Schuster, Can. J. Chem., 66 (1988) 2595; D.I. Schuster, G.E. Heibel, P.B. Brown, N.J. Turro and C.V. Kumar, J. Am. Chem. Soc., 110 (1988) 8261; D.I. Schuster, D.A. Dunn, G.E. Heibel, P.B. Brown, J.M. Rao, J. Woning and R. Bonneau, J. Am. Chem. Soc., 113 (1991) 6245.
54. [22] R. Bonneau, J. Am. Chem. Soc., 102 (1980) 3816; D.I. Schuster, R. Bonneau, D.A. Dunn, J.M. Rao and J. Joussot-Dubien, J. Am. Chem. Soc., 106 (1984) 2706; D.A. Dunn, D.I. Schuster and R. Bonneau, J. Am. Chem. Soc., 107 (1985) 2802; D. Weir, J.C. Scaiano and D.I. Schuster, Can. J. Chem., 66 (1988) 2595; D.I. Schuster, G.E. Heibel, P.B. Brown, N.J. Turro and C.V. Kumar, J. Am. Chem. Soc., 110 (1988) 8261; D.I. Schuster, D.A. Dunn, G.E. Heibel, P.B. Brown, J.M. Rao, J. Woning and R. Bonneau, J. Am. Chem. Soc., 113 (1991) 6245.
55. [22] R. Bonneau, J. Am. Chem. Soc., 102 (1980) 3816; D.I. Schuster, R. Bonneau, D.A. Dunn, J.M. Rao and J. Joussot-Dubien, J. Am. Chem. Soc., 106 (1984) 2706; D.A. Dunn, D.I. Schuster and R. Bonneau, J. Am. Chem. Soc., 107 (1985) 2802; D. Weir, J.C. Scaiano and D.I. Schuster, Can. J. Chem., 66 (1988) 2595; D.I. Schuster, G.E. Heibel, P.B. Brown, N.J. Turro and C.V. Kumar, J. Am. Chem. Soc., 110 (1988) 8261; D.I. Schuster, D.A. Dunn, G.E. Heibel, P.B. Brown, J.M. Rao, J. Woning and R. Bonneau, J. Am. Chem. Soc., 113 (1991) 6245.
56. [22] R. Bonneau, J. Am. Chem. Soc., 102 (1980) 3816; D.I. Schuster, R. Bonneau, D.A. Dunn, J.M. Rao and J. Joussot-Dubien, J. Am. Chem. Soc., 106 (1984) 2706; D.A. Dunn, D.I. Schuster and R. Bonneau, J. Am. Chem. Soc., 107 (1985) 2802; D. Weir, J.C. Scaiano and D.I. Schuster, Can. J. Chem., 66 (1988) 2595; D.I. Schuster, G.E. Heibel, P.B. Brown, N.J. Turro and C.V. Kumar, J. Am. Chem. Soc., 110 (1988) 8261; D.I. Schuster, D.A. Dunn, G.E. Heibel, P.B. Brown, J.M. Rao, J. Woning and R. Bonneau, J. Am. Chem. Soc., 113 (1991) 6245.
57. [22] R. Bonneau, J. Am. Chem. Soc., 102 (1980) 3816; D.I. Schuster, R. Bonneau, D.A. Dunn, J.M. Rao and J. Joussot-Dubien, J. Am. Chem. Soc., 106 (1984) 2706; D.A. Dunn, D.I. Schuster and R. Bonneau, J. Am. Chem. Soc., 107 (1985) 2802; D. Weir, J.C. Scaiano and D.I. Schuster, Can. J. Chem., 66 (1988) 2595; D.I. Schuster, G.E. Heibel, P.B. Brown, N.J. Turro and C.V. Kumar, J. Am. Chem. Soc., 110 (1988) 8261; D.I. Schuster, D.A. Dunn, G.E. Heibel, P.B. Brown, J.M. Rao, J. Woning and R. Bonneau, J. Am. Chem. Soc., 113 (1991) 6245.
58. [23] R.A. Caldwell and M. Singh, J. Am. Chem. Soc., 105 (1983) 5139.
59. [24] A. Weller, Z. Phys. Chem. (Wiesbaden), 133 (1982) 93.
60. [25] B.H. Lipshutz, R.S. Wilhelm, ST. Nugent, R.D. Little and MM. Baizer, J. Org. Chem., 48 (1983) 3306.
61. [26] (a) K.S. Peters, S.C. Freilich and C.G. Shaeffer, J. Am. Chem. Soc., 102 (1980) 5701; C.G. Sheafer and K.S. Peters, J. Am. Chem. Soc., 102 (1980) 7567; J.S. Simon and K.S. Peters, J. Am. Chem. Soc., 103 (1981) 6403; L.E. Manring and K.S. Peters, J. Am. Chem. Soc., 107 (1985) 6452;
62. [26] (a) K.S. Peters, S.C. Freilich and C.G. Shaeffer, J. Am. Chem. Soc., 102 (1980) 5701; C.G. Sheafer and K.S. Peters, J. Am. Chem. Soc., 102 (1980) 7567; J.S. Simon and K.S. Peters, J. Am. Chem. Soc., 103 (1981) 6403; L.E. Manring and K.S. Peters, J. Am. Chem. Soc., 107 (1985) 6452;
63. [26] (a) K.S. Peters, S.C. Freilich and C.G. Shaeffer, J. Am. Chem. Soc., 102 (1980) 5701; C.G. Sheafer and K.S. Peters, J. Am. Chem. Soc., 102 (1980) 7567; J.S. Simon and K.S. Peters, J. Am. Chem. Soc., 103 (1981) 6403; L.E. Manring and K.S. Peters, J. Am. Chem. Soc., 107 (1985) 6452;
64. [26] (a) K.S. Peters, S.C. Freilich and C.G. Shaeffer, J. Am. Chem. Soc., 102 (1980) 5701; C.G. Sheafer and K.S. Peters, J. Am. Chem. Soc., 102 (1980) 7567; J.S. Simon and K.S. Peters, J. Am. Chem. Soc., 103 (1981) 6403; L.E. Manring and K.S. Peters, J. Am. Chem. Soc., 107 (1985) 6452;
65. (b) J. D. Simon and K.S. Peters, J. Am. Chem., Soc., 106 (1984) 6452; J.D. Simon and K.S. Peters, J. Am. Chem. Soc., 105 (1983) 4875.
66. (b) J. D. Simon and K.S. Peters, J. Am. Chem., Soc., 106 (1984) 6452; J.D. Simon and K.S. Peters, J. Am. Chem. Soc., 105 (1983) 4875.
67. [27] E. Haselbach, E. Vauthey and P. Suppan, Tetrahedron, 44 (1988) 7335.
68. [28] A. Demeter, L. Biczok, T. Berces, V. Wintgens, P. Valat and J. Kossanyi, J. Phys. Chem., 97 (1993) 3217.
69. [29] E. Hayon, J. Ibata, N.N. Lichtin and M. Simic, J. Phys. Chem., 76 (1972) 2072; J. Lilie and A. Henglein, Ber. Bunsenges. Phys. Chem., 73 (1969) 170.
70. [29] E. Hayon, J. Ibata, N.N. Lichtin and M. Simic, J. Phys. Chem., 76 (1972) 2072; J. Lilie and A. Henglein, Ber. Bunsenges. Phys. Chem., 73 (1969) 170.
71. [30] S. Das and G. von Sonntag, Z. Naturforsch., 41b (1986) 505.
72. [31] D. Griller and D.D.M. Wayner, Pure Appl. Chem., (1989) 717.
73. [32] T. Hino, H. Hakazawa, H. Masuhara and N. Mataga, J. Phys. Chem., 80 (1976) 33.
74. [33] K. Dimroth, C. Reichardt, T. Siepmann and F. Bohlmann, Liebigs Ann. Chem., 1 (1963) 661.
75. [34] M.J. Kamlet, J.-L.M. Abboud, M.H. Abraham and R.W. Taft, J. Org. Chem., 48 (1983) 2877.
76. [35] S. Winstein and G.C. Robinson, J. Am. Chem. Soc., 80 (1958) 269.
77. [36] K. Mizuno, N. Ichnose and Y. Otsuji, Chem. Lett., (1985) 455; T. Tame, K. Mizuno, I. Hashita and Y. Otsuji, J. Org. Chem., 57 (1992) 5338; K. Gollnick, X.L. Xiao and V. Paulmann, J Org. Chem., 55 (1990) 5945.
78. [36] K. Mizuno, N. Ichnose and Y. Otsuji, Chem. Lett., (1985) 455; T. Tame, K. Mizuno, I. Hashita and Y. Otsuji, J. Org. Chem., 57 (1992) 5338; K. Gollnick, X.L. Xiao and V. Paulmann, J Org. Chem., 55 (1990) 5945.
79. [36] K. Mizuno, N. Ichnose and Y. Otsuji, Chem. Lett., (1985) 455; T. Tame, K. Mizuno, I. Hashita and Y. Otsuji, J. Org. Chem., 57 (1992) 5338; K. Gollnick, X.L. Xiao and V. Paulmann, J Org. Chem., 55 (1990) 5945.
80. [37] E. Hasegawa, W. Xu, P.S. Mariano, U.C. Yoon and J.U. Kim, J. Am. Chem. Soc., 110 (1988) 8099.
81. [38] V.D. Parker and M. Tilset, J. Am. Chem. Soc., 113 (1991) 8778.
82. [39] X.M. Zhang, S.R. Yeh, S. Hong, M. Freccero, A. Albini, D.E. Falvey and P.S. Mariano, J Am. Chem. Soc., 116 (1994) 4211.