Photophysical properties and photosubstitution and photoredox reactions of aromatic nitro compounds

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 2, 1996, Pages 261-274

  Nakagaki, Ryoichi ^a   Mutai, Kiyoshi ^b  

^a KANAZAWA UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001627419     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.261     Document Type: Article

References (125)

1. G. Ciamician and P. Silber, Ber. Dtsch. Chem. Ges., 33, 2911 (1900).
2. G. Ciamician and P. Silber, Ber. Dtsch. Chem. Ges., 34, 2040 (1901).
3. A. Schoenberg, "Preparative Organic Chemistry," Springer Verlag, Berlin (1968).
4. S. K. Chattopadhyay and B. B. Craig, J. Phys. Chem., 91, 323 (1987).
5. D. Gravel, J. Hebert, and D. Thoraval, Can. J. Chem., 61, 400 (1983).
6. W. N. R. Pilai, Synthesis, 1980, 1.
7. M. Wilcox, R. W. Viola, K. W. Johnson, a. P. Billington, B. K. Carpenter, J. A. McCray, A. Guzikowski, and G. P. Hess, J. Org. Chem., 55, 1585 (1990).
8. J. F. Cameron and M. J. Frechet, J. Am. Chem. Soc., 113, 4303 (1991), and references cited therein.
9. J. A. McCray and D. R. Trentham, Ann. Rev. Biophys. Chem., 18, 239 (1989).
10. S. R. Adams and R. Y. Tsien, Ann. Rev. Physiol., 55, 755 (1993).
11. J. W. Walker, G. P. Reid, J. A. McCray, and D. R. Trentham, J. Am. Chem. Soc., 110, 7170 (1988).
12. E. Reichmanis, C. W. Wilkins, Jr., and E. A. Chandross, J. Vac. Sci. Technol., 19, 1338 (1981).
13. C. W. Wilkins, Jr., E. Reichmanis, and E. A. Chandross, J. Electrochem. Soc., 129, 2252 (1982).
14. E. Reichmanis, C. W. Wilkins, Jr., and E. A. Chandross, J. Electrochem. Soc., 130, 1433 (1983).
15. E. Reichmanis, R. Gordon, C. W. Wilkins, Jr., and H. Schonhorn, J. Polym. Sci., Chem. Ed., 21, 1075 (1983).
16. P. C. Scholl and M. R. van de Mark, J. Org. Chem., 38, 2376 (1973).
17. R. Kasai, K. Shinzo, O. Tanaka, and K.-I. Kawai, Chem. Pharm. Bull., 22, 1214 (1974).
18. R. Breslow, Chem. Soc. Rev., 1, 553 (1972).
19. R. Nakagaki, Y. Tanimoto, and K. Mutai, J. Phys. Org. Chem., 6, 381 (1993), and references cited therein.
20. E. Havinga, R. O. de Jongh, and W. Dorst, Recl. Trav. Chim. Pays-Bas, 75, 378 (1956).
21. J. Cornelisse and E. Havinga, Chem. Rev., 75, 353 (1975).
22. E. Havinga and J. Cornelisse, Pure Appl. Chem., 47, 1 (1976).
23. R. Nakagaki, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 40, 651 (1982).
24. K. Mutai and R. Nakagaki, Chem. Lett., 1984, 1537.
25. K. Mutai, R. Nakagaki, and H. Tukada, Bull. Chem. Soc. Jpn., 58, 2066 (1985).
26. K. Mutai and R. Nakagaki, Bull. Chem. Soc. Jpn., 58, 3663 (1985).
27. N. J. Bunce, S. R. Cater, J. C. Scaiano, and L. J. Johnston, J. Org. Chem., 52, 4214 (1987).
28. A. Cantos, J. Marquet, and M. Moreno-Manas, Tetrahedron Lett., 28, 4191 (1987).
29. A. Cantos, J. Marquet, M. Moreno-Manas, and A. Castello, Tetrahedron, 44, 2607 (1988).
30. G. G. Wubbels, E. J. Snyder, and E. B. Coughlin, J. Am. Chem. Soc., 110, 2543 (1988).
31. J. Malkin, "Photophysical and Photochemical Properties of Aromatic Compounds," CRC Press, Boca Raton (1992).
32. H. Shizuka, N. Maeno, and K. Matsui, Mol. Photochem., 4, 335 (1972).
33. K. Mutai, S. Kanno, and K. Kobayashi, Tetrahedron Lett., 1978, 1273.
34. K. Mutai and K. Kobayashi, Bull. Chem. Soc. Jpn., 54, 462 (1981).
35. K. Mutai, K. Yokoyama, S. Kanno, and K. Kobayashi, Bull. Chem. Soc. Jpn., 55, 1112 (1982).
36. G. G. Wubbels, A. M. Halverson, and J. D. Oxman, J. Am. Chem. Soc., 102, 4849 (1980).
37. G. G. Wubbels and D. W. Celander, J. Am. Chem. Soc., 103, 7669 (1981).
38. H. A. Morrison, "The Chemistry of Nitro and Nitroso Groups," ed by H. Feuer, Wiley, New York (1969), Part 1, Chap. 4.
39. J. A. Barltrop and J. D. Coyle, "Excited States in Organic Chemistry," Wiley, New York (1975).
40. W. M. Horspool, "Aspects of Organic Photochemistry," Academic Press, London (1975).
41. N. J. Turro, "Modern Molecular Photochemistry," Benjamin/Cummings, Menlo Park (1978).
42. Y. L. Chow, "The Chemistry of Amino, Nitroso and Nitro Compounds and Their Derivatives," Wiley, New York (1982), Part 1, Supplement F, Chap. 6.
43. J. D. Coyle, "Introduction to Organic Photochemistry," Wiley, Chichester (1986).
44. E. Havinga and M. E. Kronenberg, Pure Appl. Chem., 16, 137 (1968).
45. J. Cornelisse, Pure Appl. Chem., 41, 433 (1975).
46. J. Cornelisse, G. P. de Gunst, and E. Havinga, Adv. Phys. Org. Chem., 11, 225 (1975).
47. J. Cornelisse, G. Lodder, and E. Havinga, Rev. Chem. Intermed., 2, 231 (1979).
48. a) A. N. Frolov, N. A. Kuznetsova, and A. V. El'tsov, Russ. Chem. Rev., 45, 1024 (1976);
49. b) K. Akiyama, Y. Ikegami, T. Ikenoue, and S. Tero-Kubota, Bull. Chem. Soc. Jpn., 59, 3269 (1986).
50. D. Doepp, Top. Currr. Chem., 55, 49 (1975).
51. S. Nagakura, M. Kojima, and Y. Maruyama, J. Mol. Spectrosc., 13, 174 (1964).
52. H. H. Jaffe and M. Orchin, "Theory and Applications of Ultraviolet Spectroscopy," Wiley, New York (1962).
53. B. Vidal and J. N. Murrell, Chem. Phys. Lett., 31, 46 (1975).
54. R. Hurley and A. C. Testa, J. Am. Chem. Soc., 88, 4330 (1966).
55. T. P. Carsey, G. L. Findley, and S. P. McGlynn, J. Am. Chem. Soc., 101, 4502 (1979).
56. J. N. Murrell, "The Theory of the Electronic Spectra of Organic Molecules," Methuen, London (1963).
57. S. Nagakura and J. Tanaka, J. Chem. Phys., 22, 236 (1954).
58. S. Nagakura, J. Chem. Phys., 23, 1441 (1955).
59. J. Tanaka and S. Nagakura, J. Chem. Phys., 24, 1274 (1956).
60. R. Grinter and E. Heilbronner, Helv. Chim. Acta, 45, 2496 (1962).
61. H. Labhart and G. Wagniere, Helv. Chim. Acta, 46, 1314 (1963).
62. R. Nakagaki, I. Aoyama, K. Shimizu, and M. Akagi, J. Phys. Org. Chem., 6, 251 (1993).
63. O. S. Khalil, H. G. Bach, and S. P. McGlynn, J. Mol. Spectrosc., 35, 455 (1970).
64. W. Trotter and A. C. Testa, J. Am. Chem. Soc., 90, 7044 (1968).
65. J. C. Seliskar, O. S. Khalil, and S. P. McGlynn, "Excited States," ed by E. C. Lim, Academic Press, New York (1974), Vol. 1.
66. R. Li and E. C. Lim, J. Chem. Phys., 57, 605 (1972).
67. M. Akagi, Y. Amako, and H. Azumi, Nippon Kagaku Zasshi (J. Chem. Soc. Jpn.), 87, 689 (1966).
68. J. S. Brinen and B. Singh, J. Am. Chem. Soc., 93, 6623 (1971).
69. I. Fleming, "Frontier Orbitals and Organic Chemical Reactions," Wiley, New York (1976); N. D. Epiotis and S. Shaik, J. Am. Chem. Soc., 100, 29 (1978): N. D. Epiotis, "Theory of Organic Reactions," Springer, New York (1978).
70. I. Fleming, "Frontier Orbitals and Organic Chemical Reactions," Wiley, New York (1976); N. D. Epiotis and S. Shaik, J. Am. Chem. Soc., 100, 29 (1978): N. D. Epiotis, "Theory of Organic Reactions," Springer, New York (1978).
71. I. Fleming, "Frontier Orbitals and Organic Chemical Reactions," Wiley, New York (1976); N. D. Epiotis and S. Shaik, J. Am. Chem. Soc., 100, 29 (1978): N. D. Epiotis, "Theory of Organic Reactions," Springer, New York (1978).
72. K. Mutai, S. Kanno, and K. Kobayashi, Chem. Lett., 1978, 931.
73. K. Yokoyama, R. Nakagaki, J. Nakamura, K. Mutai, and S. Nagakura, Bull. Chem. Soc. Jpn., 53, 2472 (1980).
74. K. Yokoyama, J. Nakamura, K. Mutai, and S. Nagakura, Bull. Chem. Soc. Jpn., 55, 317 (1982).
75. K. Mutai, K. Kobayashi, and K. Yokoyama, Tetrahedron, 40, 1755 (1984).
76. J. P. Maier and D. W. Turner, J. Chem. Soc., Faraday Trans. 2, 69, 521 (1973).
77. H. Ogata, H. Onizuka, Y. Nihei, and H. Kamada, Bull. Chem. Soc. Jpn., 46, 3036 (1973).
78. A. van Vliet, J. Cornelisse, and E. Havinga, Tetrahedron, 26, 1061 (1971).
79. S. Nagakura and J. Tanaka, J. Chem. Phys., 22, 563 (1954); S. Nagakura and J. Tanaka, Bull. Chem. Soc. Jpn., 32, 734 (1959); S. Nagakura, Tetrahedron, 19, Suppl. 2, 361 (1963).
80. S. Nagakura and J. Tanaka, J. Chem. Phys., 22, 563 (1954); S. Nagakura and J. Tanaka, Bull. Chem. Soc. Jpn., 32, 734 (1959); S. Nagakura, Tetrahedron, 19, Suppl. 2, 361 (1963).
81. S. Nagakura and J. Tanaka, J. Chem. Phys., 22, 563 (1954); S. Nagakura and J. Tanaka, Bull. Chem. Soc. Jpn., 32, 734 (1959); S. Nagakura, Tetrahedron, 19, Suppl. 2, 361 (1963).
82. G. G. Wubbels, B. R. Svetson, and H. Saunders, J. Am. Chem. Soc., 111, 1018 (1989).
83. K. Mutai, unpublished work; see also: G. G. Wubbels and B. R. Svetson, J. Phys. Org. Chem., 2, 177 (1989).
84. K. Mutai, unpublished work; see also: G. G. Wubbels and B. R. Svetson, J. Phys. Org. Chem., 2, 177 (1989).
85. R. Nakagaki, M. Hiramatsu, K. Mutai, and S. Nagakura, Chem. Phys. Lett., 121, 262 (1985).
86. K. Mutai, H. Tukada, and R. Nakagaki, J. Org. Chem., 56, 4896 (1991).
87. K. Mutai, Tetrahedron Lett., 1971, 1125.
88. G. G. Wubbels, B. R. Svetson, and S. N. Kaganove, Tetrahedron Lett., 27, 3103 (1986); references cited in Ref. 80; see also reviews in: Chem. Rev., 92, No. 3 (1992).
89. G. G. Wubbels, B. R. Svetson, and S. N. Kaganove, Tetrahedron Lett., 27, 3103 (1986); references cited in Ref. 80; see also reviews in: Chem. Rev., 92, No. 3 (1992).
90. K. Mutai, Y. Kajii, R. Nakagaki, and K. Obi, Tetrahedron Lett., in press.
91. K. Mutai, Bull. Chem. Soc. Jpn., 44, 25 37 (1971).
92. R. Nakagaki, H. Sakuragi, and K. Mutai, J. Phys. Org. Chem., 2, 187 (1989).
93. R. Nakagaki, K. Mutai, and S. Nagakura, Chem. Phys. Lett., 154, 581 (1989).
94. M. Takami, T. Matsuura, and I. Saito, Tetrahedron Lett., 1974, 661; D. Doepp and J. Heufer, Tetrahedron Lett., 23, 1553 (1982).
95. M. Takami, T. Matsuura, and I. Saito, Tetrahedron Lett., 1974, 661; D. Doepp and J. Heufer, Tetrahedron Lett., 23, 1553 (1982).
96. V. Jagannadham and S. Steeken, J. Am. Chem. Soc., 106, 6542 (1984).
97. R. Hurley and A. C. Testa, J. Am. Chem. Soc., 90, 1949 (1968).
98. S. Hashimoto and K. Kano, Bull. Chem. Soc. Jpn., 45, 549 (1972).
99. G. G. Wubbels, J. W. Jordan, and N. S. Mills, J. Am. Chem. Soc., 95, 1281 (1973).
100. J. A. Barltrop and N. J. Bunce, J. Chem. Soc. C, 1968, 1468.
101. W. C. Petersen and R. L. Letsinger, Tetrahedron Lett., 1971, 2197.
102. G. Porter and P. Suppan, Trans. Faraday Soc., 61, 1664 (1965).
103. K. Itoh, H. Hayashi, and S. Nagakura, Mol. Phys., 17, 561 (1969).
104. A. R. Lepley and G. L. Closs, "Chemically Induced Magnetic Polarization," Wiley, New York (1973).
105. G. L. Closs, Adv. Magn. Resort., 7, 157 (1974).
106. L. T. Muus, P. W. Atkins, K. A. MacLauchlan, and J. B. Pedersen, "Chemically Induced Magnetic Polarization," Reidel, Dordrecht (1977).
107. "Spin Polarization and Magnetic Effects in Radical Reactions," ed by Yu. N. Molin, Elsevier, Amsterdam (1984).
108. N. J. Turro, Proc. Natl. Acad. Sci. U.S.A., 80, 609 (1983).
109. U. Steiner and T. Ulrich, Chem. Rev., 89, 51 (1989).
110. R. Nakagaki, M. Hiramatsu, K. Mutai, Y. Tanimoto, and S. Nagakura. Chem. Phys. Lett., 134, 171 (1987).
111. K. Mutai, R. Nakagaki, and H. Tukada, Chem. Lett., 1987, 2261.
112. R. Nakagaki, K. Mutai, M. Hiramatsu, H. Tukada, and S. Nagakura, Can. J. Chem., 66, 1989 (1988).
113. R. Nakagaki, K. Mutai, and S. Nagakura, Chem. Phys. Lett., 167, 439 (1990).
114. Y. Ishii, H. Tukada, R. Nakagaki, and K. Mutai, Chem. Lett., 1990, 1559.
115. K. Mutai, H. Tukada, and R. Nakagaki, Bull. Chem. Soc. Jpn., 66, 920 (1993).
116. B. Brocklehurst, Int. Rev. Phys. Chem., 4, 279 (1985).
117. H. Hayashi and S. Nagakura, Bull. Chem. Soc. Jpn., 57, 322 (1984).
118. M. Okazaki, Y. Tai, K. Nunome, K. Toriyama, and S. Nagakura, Chem. Phys., 161, 177 (1992).
119. Y. Fujiwara, M. Mukai, T. Tamura, Y. Tanimoto, and M. Okazaki, Chem. Phys. Lett., 213, 89 (1993).
120. Y. Nakamura, M. Igarashi, Y. Sakaguchi, and H. Hayashi, Chem. Phys. Lett., 217, 387 (1994).
121. R. Nakagaki, O. Takahira, and K. Hiruta, Chem. Phys. Lett., 233, 41 (1995).
122. R. Nakagaki, Y. Tsujimoto, and K. Mutai, Chem. Phys. Lett., 244, 388 (1995).
123. M. Hiramatsu, R. Nakagaki, Y. Tanimoto, K. Mutai, H. Tukada, and S. Nagakura, Chem. Phys. Lett., 142, 413 (1987).
124. F. J. J. de Kanter, J. A. den Hollander, A. H. Huizer, and R. Kaptein, Mol. Phys., 34, 857 (1977).
125. "CRC Handbook of Organic Photochemistry," ed by J. C. Scaiano, CRC Press, Boca Raton (1989).