Photooxygenation of non-aromatic heterocycles

Current Organic Chemistry

Volumn 11, Issue 12, 2007, Pages 1053-1075

  Iesce, Maria Rosaria ^a   Cermola, F ^a   Rubino, M ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Biadamantylidene sulfide; Conformationally induced electrostatic stabilizati; Cycloaddition; Dehydrogenation; Nucleophilicity

Indexed keywords

AROMATIC COMPOUNDS; DEHYDROGENATION; TELLURIUM COMPOUNDS;

BIADAMANTYLIDENE SULPHIDE; CONFORMATIONALLY INDUCED ELECTROSTATIC STABILIZATI; CYCLIC COMPOUNDS; CYCLOADDITIONS; HETEROATOMS; HETEROCYCLE COMPOUNDS; HETEROCYCLES; NUCLEOPHILICITIES; PHOTOOXYGENATIONS; SILICON GERMANIUMS (SIGE);

SULFUR COMPOUNDS;

GERMANIUM; HETEROCYCLIC COMPOUND; SILICON; TELLURIUM;

ATOM; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; DEHYDROGENATION; ELECTRON TRANSPORT; OXYGENATION; PHOTOOXIDATION; REVIEW; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 34548250083     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527207781369254     Document Type: Review

References (139)

1. Ciamician, G.; Silber, P. Chem. Ber., 1912, 45, 1842.
2. Iesce, M. R.; Cermola, F.; Temussi, F. Curr. Org. Chem., 2005, 9 109.
3. Albini, A.; Freccero, M. In Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P-S., Eds.; CRC Press: Boca Raton (FL), 1995; pp. 346-357.
4. For reviews: a) Clennan, E. L.; Pace A. Tetrahedron, 2005, 61, 6665.
5. b) Gorman, A. A.; Rodgers, M. A. J. Chem. Soc. Rev., 1981, 10, 205.
6. For books: c) Foote, C. S.; Clennan, E. L. In Activa Oxygen in Chemishy; Foote, C. S.; Valentine, J. S.; Greenberg, A.; Liebman, J. F. Eds.; Chapman & Hall: Londbn, 1995; pp. 105-140.
7. d) Frimer, A. A. Singlet Oxygen, CRC Press: Boca Raton, 1985 Vol. 1-IV.
8. a) Quintero, B.; Miranda, M. A. Ars Pharm., 2000, 41, 27.
9. b) Burrows, C. J.; Muller, J. G. Chem. Rev., 998, 98, 1109.
10. c) Pratviel, G.; Bernadou, J.; Meunier, B. Angew. Chem. Int. Ed. Engl., 995, 34, 746.
11. d) Sies, H. Angew. Chem. Int. Ed. Engl., 1986, 25, 1058.
12. Iesce, M. R. In Synthetic Organic Photochemistry; Griesbeck, A. G., Mattay, J., Eds.; Marcel Dekker: New York, 2005; Vol. 12, pp. 299-363.
13. Clennan, E. L. In Synthetic Organic Photochemistry, Griesbeck, A. G., Mattay, J., Eds.; Marcel Dekker: New York, 2005; Vol. 12, pp. 365-390.
14. a) Saito, I.; Matsuura, T.; Inoue, K. J. Am. Chem. Soc., 1983, 105, 3200.
15. b) Saito, I.; Matsuura, T.; Inoue, K. J. Am. Chem. Soc., 1981, 103, 188.
16. c) Young, R. H.; Martin, R.L. J. Am. Chem. Soc., 1972, 94, 5183.
17. a) Inoue, K.; Matsuura, T.; Saito, I. Tetrahedron, 1985, 41, 2177.
18. b) Ando, W.; Nagashima, T.; Saito, K.; Khomoto, S. J. Chem. Soc. Chem. Commun., 1979, 154.
19. c) Erikson, J.; Foote, C. S.; Parker, T. L. J. Am. Chem. Soc., 1977, 99, 6455.
20. d) Foote, C.S.; Peters, J. W. J. Am. Chem. Soc., 1971, 93, 3795.
21. a) Cermola, F.; DellaGreca, M.; Iesce, M. R.; Montella, S.; Pollio, A.; Temussi, F. Chemosphere, 2004, 55, 1035.
22. b) Matsuura, T.; Yoshimura, N.; Nishinaga, A.; Saito, I. Tetrahedron, 1972, 28, 4933.
23. c) Matsuura, T.; Matsushima, M.; Kato, S.; Saito, I. Tetrahedron, 1972, 28, 5119.
24. For preceding paper see: Matsuura, T.; Saito, I. In Photochemistry of Heterocyclic Chemistry, Buchardt, O., Ed.; Wiley: New York, 1976; pp. 456-523.
25. For preceding paper see: Akasaka, T.; Ando, W. In Organic Peroxides; Ando, W., Ed.; Wiley: Chichester, 1992; pp. 599-659.
26. a) Frimer, A. A.; Bartlett, P. D.; Boschung, A. F.; Jewett, J. G. J. Am. Chem. Soc., 1977, 99, 7977.
27. b) Bartlett, P. D.; Mendenhall, G. D.; Schaap, A. P. Ann. N. Y. Acad. Sci., 1970, 171, 79.
28. Gollnick, K.; Knutzen-Mies, K. J. Org. Chem., 1991, 56, 4017.
29. Handley, R. S.; Stern, A. J.; Schaap, A. P. Tetrahedron Lett., 1985, 26, 3183.
30. Ando, W.; Kabe, Y. J. Chem. Soc. Chem. Commun., 1984, 741.
31. a) Ando, W.; Suzuki, J.; Arai, T.; Migita, T. Tetrahedron, 1972, 29, 1507.
32. b) Adam, W.; Liu, J.-C. J. Am. Chem. Soc., 1972, 94, 1205.
33. Cermola, F.; De Lorenzo, F.; Giordano, F.; Graziano, M. L.; Iesce, M. R.; Palumbo, G. Org. Lett., 2000, 2, 1205.
34. b) Cermola, F.; Iesce, M. R. J. Org. Chem., 2002, 67, 4937.
35. Iesce, M. R.; Cermola, F.; Palumbo, G.; Guaragna, A. Unpublished results.
36. Matsumoto, M.; Murakami, H.; Watanabe, N. J. Chem. Soc. Chem. Commun., 1998, 2319.
37. Matsumoto, M.; Nasu, S.; Takeda, M.; Murakami, H.; Watanabe, N. Chem. Commun., 2000, 821.
38. Lin, Y.-Y.; Li, G.-B.; Zhang, Y.-H.; Leung, H.-K. Photochem. Photobiol., 1997, 65, 82.
39. Ando, W.; Sato, R.; Yamashita, M.; Akasaka, T.; Miyazaki, H. J. Org. Chem., 1983, 48, 542.
40. Maeda, K.; Nakamura, M.; Sakai, M. J. Chem. Soc. Perkin Trans, 1983, 1, 837.
41. Mori, Y.; Maeda, K. Bull. Chem. Soc. Jpn., 1994, 67, 1204.
42. Chen, C.-W.; Shu, C.-K.; Ho, C.-T. J. Agric. Food Chem., 1996, 44, 2361.
43. Ling, K.-Q.; Cai, H.; Ye, J.-H.; Xu, J.-H. Tetrahedron, 1999, 55, 1707.
44. Avasthi, K.; Lee, S. J.; Cook, J. M.; Pickett, J. E.; Wasserman, H. H. Heterocycles, 1981, 16, 1453.
45. a) Gollnick, K.; Koegler, S.; Maurer, D. J. Org. Chem., 1992, 57, 229;
46. b) Gollnick, K.; Koegler, S. Tetrahedron Lett., 1998, 29, 1127.
47. Lemp, E.; Zanocco, A. L.; Günther, G.; Pizarro, N. J. Org. Chem., 2003, 68, 3009.
48. a) Nishio, T.; Kondo, M.; Omote, Y. J. Chem. Soc. Perkin Trans. 1, 1985, 2497.
49. b) Nishio, T.; Nishiyama, T.; Omote, Y. Tetrahedron, 1991, 47, 2979.
50. Landis, M. E.; Madoux, D. C. J. Am. Soc. Chem., 1979, 101, 5106.
51. Vargas, F.; Hisbeth, M. V.; Rojas, J. K. J. Photochem. Photobiol. A Chem., 1998, 118, 19.
52. See for example: a) Matturro, M. G.; Reynolds, R. P. Tetrahedron Lett., 1987, 28, 4981.
53. b) Gollnick, K.; Griesbeck, A. Tetrahedron Lett., 1984, 25, 4921.
54. Castedo, L.; Estevez, R. J.; Saa' J. M.; Suau, R. J. Heterocycl. Chem., 1982, 19, 1319.
55. Ando, W.; Takata, T. In Singlet Oxygen; Frimer, A. A., Ed.; CRC Press: Boca Raton, 1985; Vol. III, pp. 1-117.
56. Oae, S.; Doi, J. T. Organic Sulfur Chemistry: Structure and Mechanism, CRC Press: Boca Raton, 1991.
57. a) Jori G. In Organic Photochemistry and Photobiology, Horspool, W.; Lenci, F., Eds.; CRC Press: Boca Raton, 2004, pp. 146-(1-10).
58. b) Straight, R.C.; Spikes, J. D. In Singlet Oxygen; Frimer, A. A., Ed.; CRC Press: Boca Raton, 1985; Vol. IV, pp. 91-143.
59. Schenck, G. O.; Krauch, M. L. Angew. Chem., 1962, 74, 510.
60. See for example: Clennan, E. L. Acc. Chem. Res., 2001, 34, 875.
61. a) Jensen, F. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, 1995; Vol. 4, pp. 49-80.
62. b) Jensen, F.; Greer, A.; Clennan, E. L. J. Am. Chem, Soc., 1998, 120, 4439.
63. Baciocchi, E.; Del Giacco, T.; Elisei, F.; Gerini, M. F.; Guerra, M.; Lapi, A.; Liberali, P. J. Am. Chem. Soc., 2003, 125, 1644.
64. Liang, J.-J.; Gu, C.-L.; Kacher, M. L.; Foote, C. S. J. Am. Chem. Soc., 1983, 105, 4717.
65. Ishiguro, K.; Hayashi, M.; Sawaki, Y. J. Am. Chem. Soc., 1996, 118, 7265.
66. Toutchkine, A.; Clennan, E. L. J. Org. Chem., 1999, 64, 5620.
67. Watanabe, K. N.; Ishiguro, K.; Sawaki, Y. J. Am. Chem. Soc., 1991, 113, 2677.
68. Clennan, E. L.; Greer, A. J. Org. Chem., 1996, 61, 4793.
69. Gu, C.-L.; Foote, C. S.; Kacher, M. L. J. Am. Chem. Soc., 1981, 103, 5949.
70. Bonesi, S.M.; Albini, A. J. Org. Chem., 2000, 65, 4532.
71. Clennan, E. L.; Wang, D.-X.; Jang, K.; Hodgson, D. J.; Oki, A. R. J. Am. Chem. Soc., 1992, 114, 3021.
72. Sawaki, Y.; Ogata, Y. J. Am. Chem. Soc., 1981, 103, 5947.
73. Takata, T.; Hoshino, K.; Takeuchi, E.; Tamura, Y.; Ando, W. Tetrahedron Lett., 1984, 42, 4767.
74. a) Corey, E. J.; Ouannes, C. Tetrahedron Lett., 1976, 17, 4263.
75. b) Bonesi, S. M.; Torriani, R.; Mella, M.; Albini, A. Eur. J. Org. Chem., 1999, 1723.
76. c) Toutchkine, A.; Aebisher, D.; Clennan, E. L. J. Am. Chem. Soc., 2001, 123, 4966.
77. Akasaka, T.; Sakurai, A.; Ando, W. J. Am. Chem. Soc., 1991, 113, 2696.
78. Clennan, E. L.; Aebisher, D. J. Org. Chem., 2002, 67, 1036.
79. a) Clennan, E. L.; Hightower, S. E. J. Org. Chem., 2006, 71, 1247.
80. b) Clennan, E. L.; Hightower, S. E.; Greer, A. J. Am. Chem. Soc., 2005, 127, 11819.
81. Jensen, F.; Foote, C. S. J. Am. Chem. Soc., 1987, 109, 1478.
82. Ando, W.; Sonobe, H.; Akasaka, T. Tetrahedron Lett. 1986, 27, 4473.
83. Clennan, E. L.; Dobrowoski, P.; Greer, A. J. Am. Chem. Soc., 1995, 117, 9800.
84. Takata, T.; Ishibashi, K.; Ando, W. Tetrahedron Lett., 1985, 26, 4609.
85. Takata, T.; Tamura, Y.; Ando, W. Tetrahedron, 1985, 41, 2133.
86. Barbarella, G.; Garbesi, A.; Fava, A. Helv. Chim. Acta, 1971, 51, 2297.
87. Duthaler, R. O. Angew. Chem. Int. Ed. Engl., 1991, 30, 705.
88. Toutchkine, A.; Clennan, E. L. Tetrahedron Lett., 1999, 40, 6519.
89. Pandey, B.; Bal, S. Y.; Khire, U. R.; Rao, A.T. J. Chem. Soc. Perkin Trans. 1, 1990, 3217.
90. a) Pandey, B.; Bal, S. Y.; Khire, U. R. Tetrahedron Lett., 1989, 30, 4007.
91. b) Kamata, M.; Sato, M.; Hasegawa, E. Tetrahedron Lett., 1992, 33, 5085.
92. Takahashi, T. T.; Nakamura, C. Y.; Satob, S. Y. J. Chem. Soc. Chem. Commun., 1977, 680.
93. Geller, G. G.; Foote, C. S.; Pechman, D. B. Tetrahedron Lett., 1983, 24, 673.
94. Sheu, C.; Foote, C. S.; Gu, C.-L. J. Am. Chem. Soc., 1992, 114; 3015.
95. Akasaka, T.; Ando, W. Tetrahedron Lett., 1985, 26, 5049.
96. a) Smith, W. F. J. Am. Chem. Soc., 1972, 94, 186.
97. b) Ogryzlo, E. A.; Tang, C. W. J. Am. Chem. Soc., 1970, 92, 5034.
98. c) Ouannes, C.; Wilson, T., J. Am. Chem. Soc., 1968, 92, 6527.
99. a) Fisch, M. H.; Graham, J. C.; Olesen, J. A. J. Chem. Soc. Chem. Commun., 1971, 663.
100. b) Fisch, M. H.; Gramain, J, C., Oleson, J. A. J. Chem. Soc. Chem. Commun., 1970, 13.
101. Schaefer, F. C.; Zimmerman W. D. J. Org. Chem., 1970, 35, 2165.
102. a) Bartholomew, R. F.; Davidson, R. S. J. Chem. Soc. Chem. Commun., 1970, 1174.
103. b) Schenk, G. O. Angew. Chem., 1957, 69, 579.
104. Gramain, J.-C.; Remusen, R.; Troin, Y. Tetrahedron, 1979, 35, 759.
105. b) Gramain, J.-C.; Remusen, R.; Troin, Y. J. Chem. Soc., Chem. Commun., 1976, 194.
106. See for example: Yoshioka, M.; Sakuma, Y.; Saito, M. J. Org. Chem., 1999, 64, 9247 and references therein.
107. a) Ling, K.-Q.; Ye, J.-H.; Chen, X.-Y.; Ma, D.-J.; Xu, J.-H. Tetrahedron, 1999, 55, 9185.
108. b) Ke-Qing, L.; Gang, J.; Hu, C.; Jian-Hua, X. Tetrahedron Lett., 1998, 39, 2381.
109. Cocquet, G.; Ferroud, C.; Guy, A. Tetrahedron, 2000, 56, 2975.
110. Ferroud, C.; Cocquet, G.; Guy, A. Tetrahedron Lett., 1999, 40, 5005.
111. Cocquet, G.; Ferroud, C.; Simon, P.; Taberna, P.-L. J. Chem. Soc., Perkin Trans. 2, 2000, 1147.
112. a) Bhat, V.; George, M. V. Tetrahedron Lett., 1977, 4133.
113. b) Bhat, V.; George, M. V. J. Org. Chem., 1979, 44, 3288.
114. a) Schaap, A. P.; Prasad, G.; Siddiqui, S. Tetrahedron Lett., 1984, 25, 3035.
115. b) Schaap, A. P.; Prasad, G.; Gagnon, S. D. Tetrahedron Lett., 1983, 24, 3047.
116. a) Futamara, S.; Kusunose, S.; Ohta, H.; Kamiya, Y. J. Chem. Soc. Perkin Trans. 1, 1984, 15.
117. b) Futamara, S.; Kusunose, S.; Ohta, H.; Kamiya, Y. J. Chem. Soc. Chem. Commun., 1982, 1223.
118. a) Schaap, A. P.; Siddiqui, S.; Prasad, G.; Palomino, E.; Sandison, M. Tetrahedron, 1985, 41, 2229.
119. b) Schaap, A. P.; Siddiqui, S.; Gagnon, S. D.; Lopez, L. J. Am. Chem. Soc., 1983, 105, 5149.
120. c) Schaap, A. P.; Lopez, L.; Gagnon, S. D. J. Am. Chem. Soc., 1983, 105, 663.
121. a) Eriksen, J.; Foote, C. S. J. Phys. Chem., 1978, 82, 2659.
122. b) Eriksen, J.; Foote, C. S.; Parker, T. L. J. Am. Chem. Soc., 1977, 99, 6455.
123. Miyashi, T.; Kamata. M.; Mukai, T. J. Chem. Soc. Chem. Commun., 1986, 1577.
124. West, R. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1989; Vol. 2, pp. 1207-1240.
125. Long, C.; Pryce, M. T. In The Chemistry of Organic Germanium, Tin and Lead Compounds; Rappoport; Z., Ed.; John Wiley and Sons: Chicester, 2002, Vol. 2, pp. 1521-1542.
126. a) Nakadaira, Y.; Nomura, T.; Kanouchi, S.; Sato, C.; Kabuto, C.; Sakurai, H. Chem. Lett., 1983, 209.
127. b) Sato, T.; Moritani, I.; Matsuyama, M. Tetrahedron Lett., 1969, 58, 5113.
128. Akasaka, T.; Sato, K.; Kako, M.; Ando, W. Tetrahedron Lett., 1991, 32, 6605.
129. Ando, W.; Kako, M.; Akasaka, T. J. Chem. Soc. Chem. Commun., 1992, 458.
130. Nakadaira, Y.; Sakurai, H. J. Organomet. Chem., 1973, 47, 61.
131. Mochida, K.; Akazawa, M.; Fijitsuka, M.; Watanabe, A.; Ito, O. Bull. Chem. Soc. Jpn., 1997, 70, 2249.
132. a) Ando, W.; Kako, M.; Akasaka, T.; Kabe, Y. Tetrahedron Lett, 1990, 31, 4177.
133. b) Ando, W.; Kako, M.; Akasaka, T.; Nagase, S.; Kawai, T.; Nagai, Y.; Sato, T. Tetrahedron Lett., 1989, 30, 6705.
134. Kako, M.; Akasaka, T.; Ando, W. J. Chem. Soc. Chem. Commun., 1992, 457.
135. Goldschmidt, Z. The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S. Ed.; John Wiley: Chichester, 1987; Vol. 2, pp. 275-337.
136. Luppold, E.; Winter, W.; Muller, E. Chem. Ber., 1976, 109, 3886.
137. Detty, M. R.; Merkel, P. B.; Powers, S. K. J. Am. Chem. Soc., 1988, 110, 5920.
138. Dougherty, T. J.; Levy, J. G. In Organic Photochemistry and Photobiology, Horspool, W.; Lenci, F., Eds.; CRC Press: Boca Raton, 2004, pp. 147-(1-17).
139. Tsao, R; Eto, M. In Aquatic and Surface Photochemistry, Helz, G. R.; Zepp, R. G.; Crosby, D. G., Eds.; Lewis: London; 1994, pp. 163-171.