Photoinduced electron-transfer oxidation of olefins with molecular oxygen sensitized by tetrasubstituted dimethoxybenzenes: A non-singlet-oxygen mechanism

Helvetica Chimica Acta

Volumn 84, Issue 9, 2001, Pages 2693-2707

  Mori, Tadashi ^a   Takamoto, Makolo ^a   Wada, Takehiko ^a   Inoue, Yoshihisa ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENCE; OLEFINS; ORGANIC COMPOUNDS; OXYGEN; POSITIVE IONS;

PHOTODURABILITY;

OXIDATION;

ALKENE DERIVATIVE; BENZENE DERIVATIVE; DIMETHOXYBENZENE DERIVATIVE; KETONE DERIVATIVE; OXYGEN; SUPEROXIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ELECTRON TRANSPORT; FLUORESCENCE; OXIDATION; PHOTOCHEMISTRY; PHOTOOXIDATION; QUANTUM CHEMISTRY;

EID: 0034760858     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1522-2675(20010919)84:9<2693::AID-HLCA2693>3.0.CO;2-3     Document Type: Article

References (89)

1. a) S. Vasenkov, H. Frei, Mol. Supramol. Photochem. 2000, 5, 295;
2. b) C. Tanielian, R. Mechin, R. Seghrouchni, C. Schweitzer, Photochem. Photobiol. 2000, 71, 12;
3. c) N. Satoh, S. Fukuzumi, Rev. Heteroat. Chem. 1999, 20, 249;
4. d) T. Tanaka, H. Yoshida, Hyomen Kagaku 1999, 20, 73;
5. e) H. Frei, Brookhaven Natl. Lab., [Rep.] BNL 1995, 61733, 18;
6. f) T. Akasaka, W. Ando, Yuki Gosei Kagaku Kyokaishi 1993, 51, 212;
7. g) L. Lopez, Top. Cur. Chem. 1990, 156, 117;
8. h) M. A. Fox, in 'Photoinduced Electron Transfer, Vol. Pt. D,' Ed. M. A. Fox, M. Chanon, Elsevier, Amsterdam, Netherlands, 1988, pp. 1;
9. i) K. H. Pfoertner, Spec. Publ.-R. Soc. Chem. 1986, 57, 189;
10. j) C. S. Foote, Tetrahedron 1985, 41, 2221;
11. k) J. F. Rabek, Wiad. Chem. 1971, 25, 435.
12. a) B. Ranby, J. F. Rabek, 'Photodegradation, Photooxidation and Photostabilization of Polymers', Wiley, London, 1975;
13. b) M. S. A. Abdou, S. Holdcroft, Macromolecules 1993, 26, 2954;
14. c) R. D. Scurlock, B. Wang, P. R. Ogilby, R. L. Clough, J. Am. Chem. Soc. 1995, 117, 10194;
15. d) M. J. Thomas, C. S. Foote, Photochem. Photobiol. 1978, 27, 687;
16. e) R. W. Denny, A. Nickon, Org. React. 1973, 20, 133.
17. M. Stratakis, M. Orfanopoulos, Tetrahedron 2000, 56, 1595.
18. a) C. S. Foote, Acc. Chem. Res. 1968, 1, 104;
19. b) L. M. Stephenson, M. J. Grdina, M. Orfanopoulos, Acc. Chem. Res. 1980, 13, 419;
20. c) C. S. Foote, E. L. Clennan, in 'Active Oxygen in Chemistry,' Ed. C. S. Foote, J. S. Valentine, A. Greenberg, J. F. Liebman, Chapman & Hall, London, 1995, p 105;
21. d) A. A. Frimmer, L. M. Stephanson, in 'Singlet Oxygen. Reactions, Modes and Products,' Ed. A. A. Frimer, CRC Press, Boca Raton, FL, 1985;
22. e) H. H. Wasserman, J. L. Ives, Tetrahedron 1981, 37, 1825;
23. f) H. H. Wasserman, R. W. Murray, in 'Singlet Oxygen,' Academic Press, New York, 1979.
24. E. A. Lissi, M. V. Encinas, E. Lemp, M. A. Rubio, Chem. Rev. 1993, 93, 699.
25. a) J. Eriksen, C. S. Foote, T. L. Parker, J. Am. Chem. Soc. 1977, 99, 6455;
26. b) K. A. Zaklika, B. Kaskar, A. P. Schaap, J. Am. Chem. Soc. 1980, 102, 386;
27. c) A. P. Schaap, K. A. Zaklika, B. Kaskar, W.-M. Fung, J. Am. Chem. Soc. 1980, 102, 389;
28. d) L. T. Spada, C. S. Foote, J. Am. Chem. Soc. 1980, 102, 391.
29. a) C. S. Foote, J. W. P. Liu, Tetrahedron Lett. 1968, 326;
30. b) C. S. Foote, A. A. Dzakapasu, J. W. P. Liu, Tetrahedron Lett. 1975, 1247.
31. a) T. J. Dougherty, Photochem. Photobiol. 1987, 45, 879;
32. b) J. J. McCullough, Chem. Rev. 1987, 87, 811.
33. a) T. Kubo, T. Inoue, H. Sakai, J. Am. Chem. Soc. 1992, 114, 7660;
34. b) H. J. P. de Lijser, D. R. Arnold, J. Org. Chem. 1997, 62, 8432;
35. c) K. Mizuno, R. Kaji, Y. Otsuji, Chem. Lett. 1977, 1027;
36. d) N. C. Yang, D. M. Shold, J. K. McVey, J. Am. Chem. Soc. 1975, 97, 5004;
37. e) N. C. Yang, K. Srinivasachar, B. Kim, J. Libman, J. Am. Chem. Soc. 1975, 97, 5006.
38. a) C. Tanielian, C. Wolff, J. Phys. Chem. 1995, 99, 9825;
39. b) D. Murtinho, M. Pineiro, M. M. Pereira, A. M. d'A. R. Gonsalves, L. G. Arnaut, M. da Graa Miguel, H. D. Burrows, J. Chem. Soc., Perkin Trans. 2 2000, 2441.
40. T. H. W. Poon, K. Pringle, C. S. Foote, J. Am. Chem. Soc. 1995, 117, 7611.
41. T. Mori, M. Takamoto, Y. Tate, J. Shinkuma, T. Wada, Y. Inoue, Tetrahedron Lett. 2001, 42, 2505.
42. D. R. Kearns, W. Fenical, P. Radlick, Ann. N. Y. Acad. Sci. 1970, 171, 34.
43. L. E. Manring, J. Eriksen, C. S. Foote, J. Am. Chem. Soc. 1980, 102, 4275.
44. U. T. Bhalerao, M. Sridhar, Tetrahedron Lett. 1993, 34, 4341.
45. R. Rathore, J. K. Kochi, J. Org. Chem. 1994, 60, 4399.
46. M. A. J. Rodgers, J. Am. Chem. Soc. 1983, 105, 6201.
47. C. S. Foote, in 'Singlet Oxygen', Academic Press, New York, 1979, p. 139;
48. b) C. Ovannés, T. Wilson, J. Am. Chem. Soc. 1968, 90, 6528;
49. c) H. Görner, D. Schulte-Frohlinde, Chem. Phys. Lett. 1986, 124, 321.
50. A. Greer, G. Vassilikogiannakis, K.-C. Lee, T. S. Koffas, K. Nahm, C. S. Foote, J. Org. Chem. 2000, 65, 6876.
51. S. M. Bonesi, M. Mella, N. d'Alessandro, G. G. Aloisi, M. Vanossi, A. Albini, J. Org. Chem. 1998, 63, 9946.
52. T. Mori, T. Wada, Y. Inoue, Org. Lett. 2000, 2, 3401.
53. a) N. Hoffmann, J.-P. Pete, J. Org. Chem. 1997, 62, 6952;
54. b) N. Hoffmann, J.-P. Pete, Tetrahedron Lett. 1998, 39, 5027;
55. c) J.-H. Ho, T-I. Ho, R. S. H. Liu, Org. Lett. 2001, 3, 409.
56. a) S. Hashimoto, H. Akimoto, J. Phys. Chem. 1987, 91, 1347;
57. b) F. Blatter, F. Moreau, H. Frei, J. Phys. Chem. 1994, 98, 13403;
58. c) H. Sun, F. Blatter, H. Frei, ACS Symp. Ser. 1996, 638, 409;
59. d) T. Kodaira, K. Hayashi, T. Ohnishi, Polym. J. 1973, 4, 1;
60. e) D. G. M. Wood, T. M. Kollmau, Chem. Ind. 1972, 423.
61. a) D. Rehm, A. Weller, Isr. J. Chem. 1970, 8, 259;
62. b) D. Rehm, A. Weller, Z. Phys. Chem. 1970, 69, 183.
63. R. Rathore, E. Bosch, J. K. Kochi, Tetrahedron 1994, 50, 6727.
64. 'Handbook of Photochemistry', 2nd edn., Ed. S. L. Murov, I. Carmichael, G. L. Hug, Marcel Dekker, Inc., New York, 1993.
65. 'DMS UV Atlas of Organic Compounds', Ed. H.-H. Perkampus, I. Sandeman, C. J. Timons, Verlag Chemie, Weinheim, Butterworths, London, 1966-71.
66. a) D. P. R. Muller, M. A. Goss-Sampson, Crit. Rev. Neurobiol. 1990, 5, 239;
67. b) G. W. Burton, A. Joyce, K. U. Ingold, Arch. Biochem. Biophys. 1983, 221, 281;
68. c) M. T. Craw, M. C. Depew, Rev. Chem. Intermed. 1985, 6, 1;
69. d) S. Sur, J. P. Colpa, Chem. Phys. Lett. 1986, 127, 577.
70. C. Reichardt, Angew. Chem., Int. Ed. 1979, 18, 78.
71. a) A. L. Tappel, Vitam. Horm. (N. Y.) 1962, 20, 493;
72. b) P. P. Nair, R. N. Patnaik, J. W. Hauswirth, in 'Tocopherol, Oxygen and Biomembranes', Ed. C Deduve, O. Hayashi, Elsevier Press, New York, 1978, 121;
73. c) K. A. Fukuzawa, A. Tokumura, S. Ouchi, H. Tsukatani, Lipids 1982, 511.
74. C. Shi, F. C. Anson, J. Electroanal. Chem. 2000, 484, 144.
75. a) T. Kanno, T. Oguchi, H. Sakaragi, K. Takamoku, Tetrahedron Lett. 1980, 21, 467;
76. b) M. A. Fox, C. C. Chen, J. Am. Chem. Soc. 1981, 103, 6757;
77. c) M. A. Fox, J. N. Younathan, Tetrahedron 1986, 42, 6285;
78. d) Y. Taniguhi, A. Mioshi, N. Mataga, H. Shizuka, T. Morita, Chem. Phys. Lett. 1972, 15, 2223.
79. P. D. Bartlett, Chem. Soc. Rev. 1976, 149.
80. J. Eriksen, C. S. Foote, J. Am. Chem. Soc. 1980, 102, 6083.
81. a) C. W. Jefford, A. F. Boschung, Helv. Chim. Acta 1977, 60, 2673;
82. b) A. P. Schaap, G. R. Faler, J. Am. Chem. Soc. 1973, 95, 3381.
83. a) D. H. R. Barton, G. Leclerc, P. D. Magnus, I. D. Menzics, J. Chem. Soc., Chem. Commun. 1972, 447;
84. b) S. F. Nelsen, R. Akaba, J. Am. Chem. Soc. 1981, 103, 2096;
85. c) S. F. Nelsen, D. L. Kapp, R. Akaba, D. H. Evans, J. Am. Chem. Soc. 1986, 108, 6863.
86. W. H. Richardson, F. C. Montgomery, M. B. Yelvington, H. E. O'Neal, J. Am. Chem. Soc. 1974, 96, 7525.
87. 'Purification of Laboratory Chemicals', 4th edn., Ed. W. L. F. Ararego, D. D. Perrin, Reed Educational and Professional Publishing Ltd, Oxford, 1996.
88. R. J. MacLeod, A. L. Pincock, J. A. Pincock, K. A. Thompson, J. Am. Chem. Soc. 1998, 120, 6443.
89. J. N. Demas, G. A. Crosby, J. Phys. Chem. 1971, 75, 991.