Photoinitiated domino reactions: N-(adamantyl)phthalimides and N-(adamantylalkyl)phthalimides

Journal of Organic Chemistry

Volumn 74, Issue 21, 2009, Pages 8219-8231

  Horvat, Margareta ^a   Görner, Helmut ^b   Warzecha, Klaus Dieter ^b   Neudörfl, Jörg ^c   Griesbeck, Axel G ^c   Mlinarić Majerski, Kata ^a   Basarić, Nikola ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

^b MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

^c UNIVERSITY OF COLOGNE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

A-THERMAL; ADAMANTANES; ADAMANTYL GROUPS; CHEMICAL EQUATIONS; DIRECT IRRADIATION; DOMINO REACTIONS; ELECTROCHEMICAL MEASUREMENTS; EXCITED SINGLET STATE; EXCITED TRIPLET STATE; H-ABSTRACTION; INTERMOLECULAR ELECTRON TRANSFER; INTRA-MOLECULAR ELECTRON TRANSFER; NEW PRODUCT; PHOTOPRODUCTS; PHTHALIMIDE; RADICAL ANIONS; TRIETHYLAMINES; TRIPLET SENSITIZATION; TRIPLET STATE;

ABSTRACTING; ACETONE; ELECTRON TRANSITIONS; FREE RADICAL REACTIONS; REACTION KINETICS;

PHOTOCHEMICAL REACTIONS;

1,4 DIAZABICYCLO[2.2.2]OCTANE; ACETONE; ADAMANTANE DERIVATIVE; ANION; BENZAZEPINE DERIVATIVE; HYDROGEN; PHTHALIMIDE DERIVATIVE; SOLVENT; TRIETHYLAMINE;

ARTICLE; CHEMICAL REACTION; ELECTROCHEMISTRY; ELECTRON TRANSPORT; IRRADIATION; PHOTOCHEMISTRY; SENSITIZATION;

ELECTROCHEMISTRY; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PHOTOCHEMISTRY; PHTHALIMIDES; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 70350733548     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901753z     Document Type: Article

References (113)

1. (a) Multicomponent Reactions; Zhu, J., Bienaymé, H., Eds.; Wiley-WCH: Weinheim, 2005.
2. (b) Tejedor, D.; Garcķa-Tellado, F. Chem. Soc. Rev. 2007, 36, 484-491.
3. (c) Dömling, A. Chem. Rev. 2006, 106, 17-89.
4. (d) Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602-1634.
5. (e) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
6. (a) Tietze, L. F.; Brasche, G.; Gericke, K. Domino Reactions in Organic Synthesis; Wiley-WCH: Weinheim, 2006.
7. (b) Müller, T. J. J.; D'Souza, D. M. Pure Appl. Chem. 2008, 80, 609-620.
8. (c) Hu, Q.-S. Synlett 2007, 1331-1345.
9. (d) Padwa, A.; Bur, S. K. Tetrahedron 2007, 63, 5341-5378.
10. (e) Langer, P. Synlett 2007, 1016-1025.
11. (f) Enders, D.; Grondal, C.; Huettl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570-1581.
12. (g) Pellissier, H. Tetrahedron 2006, 62, 2143-2173.
13. (h) Pellissier, H. Tetrahedron 2006, 62, 1619-1665.
14. (i) de Meijere, A.; von Zezschwitz, P.; Braese, S. Acc. Chem. Res. 2005, 38, 413-422.
15. (j) Tietze, L. F.; Rackelmann, N. Pure Appl. Chem. 2004, 76, 1967-1983.
16. (k) Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
17. (l) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. 1993, 32, 131-161.
18. (a) Quinkert, G.; Stark, H. Angew. Chem., Int. Ed. 1983, 22, 637-655.
19. (b) Quinkert, G.; Schwartz, U.; Stark, H.; Weber, W.-D.; Adam, F.; Beier, H.; Frank, G.; Dürner, G. Liebigs Ann. Chem. 1982, 1999-2040.
20. Wender, P. A.; Singh, S. K. Tetrahedron Lett. 1990, 31, 2517-2520.
21. Golobish, T. D.; Burke, J. K.; Kim, A. H.; Chong, S. W.; Probst, E. L.; Carroll, P. J.; Dailey, W. P. Tetrahedron 1998, 54, 7013-7024.
22. Nair, V.; Anikumar, G.; Jayan, N. C.; Rath, N. P. Tetrahedron Lett. 1998, 39, 2437-2440.
23. (a) Waske, P. A.; Mattay, J. Tetrahedron 2005, 61, 10321-10330.
24. (b) Bunte, J. O.; Rinne, S.; Mattay, J. Synthesis 2004, 619-633.
25. (a) Büchi, G.; Carlson, J. A.; Powell, J. E., Jr.; Tietze, L. F. J. Am. Chem. Soc. 1970, 92, 2165-2167.
26. (b) Partridge, J. J.; Chadha, N. K.; Uskokovic, M. R. J. Am. Chem. Soc. 1973, 95, 532-540.
27. (c) Tietze, L. F.; Glüsenkamp, K.-H.; Nakane, M.; Hutchinson, C. R. Angew. Chem., Int. Ed. 1982, 21, 70-71.
28. (a) Tietze, L. F.; Brüggemann, K. Angew. Chem., Int. Ed. 1979, 18, 540-541.
29. (b) Tietze, L. F.; Bergmann, A. Angew. Chem., Int. Ed. 1985, 24, 127-128.
30. (c) Tietze, L. F.; Bergmann, A.; Brüggemann, K. Synthesis 1986, 190-192.
31. Basarić, N.; Horvat, M.; Mlinarić-Majerski, K.; Zimmermann, E.; Neudörfl, J.; Griesbeck, A. G. Org. Lett. 2008, 10, 3965-3968.
32. Basarić, N.; Horvat, M.; Franković, O.; Mlinarić-Majerski, K.; Neudörfl, J.; Griesbeck, A. G. Tetrahedron 2009, 65, 1438-1443.
33. (a) Leedy, D. W.; Muck, D. L. J. Am. Chem. Soc. 1971, 93, 4264-4275.
34. (b) Coyle, J. D.; Newport, G. L.; Harriman, A. J. Chem. Soc., Perkin Trans. 2 1978, 133-137.
35. (c) Coyle, J. D.; Harriman, A.; Newport, G. L. J. Chem. Soc., Perkin Trans. 2 1979, 799-802.
36. (d) Filho, P. B.; Toscano, V. G.; Politi, M. J. J. Photochem. Photobiol. A: Chem. 1988, 43, 51-58.
37. (e) Almeida, F. C. L.; Toscano, V. G.; dos Santos, O.; Politi, M. J.; Neumann, M. G.; Fo, P. B. J. Photochem. Photobiol. A: Chem. 1991, 58, 289-294.
38. (f) Valat, P.; Wintgens, V.; Kossanyi, J.; Biczók, L.; Demeter, A.; Bérces, T. J. Am. Chem. Soc. 1992, 114, 946-953.
39. (g) Wingtens, V.; Valat, P.; Kossanyi, J.; Biczók, L.; Demeter, A.; Bérces, T. J. Chem. Soc. Faraday Trans. 1994, 90, 411-421.
40. (a) Griesbeck, A. G.; Görner, H. J. Photochem. Photobiol. A: Chem. 1999, 129, 111-119.
41. (b) Görner, H.; Griesbeck, A. G.; Heinrich, T.; Kramer, W.; Oelgemöller, M. Chem. Eur. J. 2001, 7, 1530-1538.
42. (c) Görner, H.; Oelgemöller, M.; Griesbeck, A. G. J. Phys. Chem. A 2002, 106, 1458-1464.
43. (d) Warzecha, K.-D.; Görner, H.; Griesbeck, A. G. J. Phys. Chem. A 2006, 110, 3356-3363.
44. Kanaoka, Y.; Migita, Y.; Koyama, K. Tetrahedron Lett. 1973, 14, 1193-1196.
45. (a) Griesbeck, A. G.; Kramer, W.; Oelgemöller, M. Synlett 1999, 1169-1178.
46. (b) Griesbeck, A. G.; Heinrich, T.; Oelgemöller, M.; Lex, J.; Molis, A. J. Am. Chem. Soc. 2002, 124, 10972-10973.
47. (c) Soldevilla, A.; Griesbeck, A. G. J. Am. Chem. Soc. 2006, 128, 16472-16473.
48. (d) Griesbeck, A. G.; Hoffmann, N.; Warzecha, K.-D. Acc. Chem. Res. 2007, 40, 128-140.
49. (a) Yoon, U. C.; Oh, S. W.; Lee, J. H.; Park, J. H.; Kang, K. T.; Mariano, P. S. J. Org. Chem. 2001, 66, 939-943.
50. (b) Yoon, U. C.; Jin, Y. X.; Oh, S. W.; Park, C. H.; Park, J. H.; Campana, C. F.; Cai, X.; Duesler, E. N.; Mariano, P. S. J. Am. Chem. Soc. 2003, 125, 10664-10671.
51. (c) Yoon, U. C.; Kwon, H. C.; Hyung, T. G.; Choi, K. H.; Oh, S. W.; Yang, S.; Zhao, Z.; Mariano, P. S. J. Am. Chem. Soc. 2004, 126, 1110-1124.
52. (d) Cho, D. W.; Choi, J. H.; Oh, S. W.; Quan, C.; Yoon, U. C.; Wang, R.; Yang, S.; Mariano, P. S. J. Am. Chem. Soc. 2008, 130, 2276-2284.
53. (a) Mauder, H.; Griesbeck, A. G. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P.-S., Eds.; CRC Press: Boca Ranton, 1995; pp 513-521.
54. (b) Griesbeck, A. G. Liebigs Ann. 1996, 1951-1958.
55. (c) Griesbeck, A. G. Chimia 1998, 52, 272-283.
56. (d) Oelgemöller, M.; Griesbeck, A. G. J. Photochem. Photobiol. C: Photochem. Rev. 2002, 3, 109-127.
57. (e) Oelgemöller, M.; Griesbeck, A. G. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Lenci, F., Eds.; CRC Press: Boca Raton, FL, 2004; pp 1-19.
58. (a) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407-413.
59. (b) Coyle, J. D. In Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum Press: New York, 1984; pp 259-284.
60. (c) Mazzocchi, P. H. Org. Photochem. 1981, 5, 421-471.
61. (d) Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 2001, 34, 523-533.
62. (e) McDermott, G.; Yoo, D. J.; Oelgemöller, M. Heterocycles 2005, 65, 2221-2257.
63. (a) Mlinarić-Majerski, K.; Pavlović, D.; Milinković, V.; Kojić-Prodić, B. Eur. J. Org. Chem. 1998, 1231-1236.
64. (b) Mlinarić-Majerski, K.; Kragol, G. Eur. J. Org. Chem. 1999, 1401-1406.
65. (c) Mlinarić-Majerski, K.; Veljković, J.; Kaselj, M.; Marchand, A. P. Eur. J. Org. Chem. 2004, 2923-2927.
66. (d) Šafar-Cvitaš, D.; Savin, B.; Mlinarić-Majerski, K. Croat. Chem. Acta 2004, 77, 619-625.
67. (e) Mlinarić-Majerski, K.; Margeta, R.; Veljković, J. Synlett 2005, 2089-2091.
68. (f) Matković, M.; Veljković, J.; Mlinarić-Majerski, K.; Molčanov, K.; Kojić-Prodić, B. J. Mol. Struct. 2007, 832, 191-198.
69. (g) Basarić, N.; Molčanov, K.; Matković, M.; Kojić-Prodić, B.; Mlinarić-Majerski, K. Tetrahedron 2007, 63, 7985-7996.
70. (h) Mlinarić-Majerski, K.; Kragol, G.; Sumanovac Ramljak, T. Synlett 2008, 405-409.
71. (i) Vujasinović, I.; Veljković, J.; Molčanov, K.; Kojić-Prodić, B.; Mlinarić-Majerski, K. J. Org. Chem. 2008, 73, 9221-9227.
72. (a) Mlinarić-Majerski, K.; Veljković, J.; Marchand, A. P.; Ganguly, B. Tetrahedron 1998, 54, 11381-11386.
73. (b) Marchand, A. P.; Kumar, K. A.; Mlinarić-Majerski, K; Veljković, J. Tetrahedron 1998, 54, 15105-15112.
74. (c) Marchand, A. P.; Alihodžić, S.; McKim, A. S.; Kumar, K. A.; Mlinarić-Majerski, K.; Šumanovac, T.; Bott, S. G. Tetrahedron Lett. 1998, 39, 1861-1864.
75. (d) Mlinarić-Majerski, K.; Veljković, J.; Kaselj, M. Croat. Chem. Acta 2000, 73, 575-584.
76. (a) Lundahl, K.; Schut, J.; Schlatmann, J. L. M. A.; Paerels, G. B.; Paters, A. J. Med. Chem. 1972, 15, 129-136.
77. (b) Kolocouris, N.; Foscolos, G. B.; Kolocouris, A.; Marakos, P.; Pouli, N.; Fytas, G.; Ikeda, S.; De Clerq, E. J. Med. Chem. 1994, 37, 2896-2902.
78. (c) Kolocouris, N.; Kolocouris, A.; Foscolos, G. B.; Fytas, G.; Neyts, J.; Padalko, E.; Balzarini, J.; Snoeck, R.; Andrei, G.; De Clerq, E. J. Med. Chem. 1996, 39, 3307-3318.
79. Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1998, 120, 12755-12769.
80. (a) Arts, N. B. M.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron 1978, 34, 1271-1279.
81. (b) Burks, J. E., Jr.; Crandall, J. K. J. Org. Chem. 1984, 49, 4663-4670.
82. (c) Forward, P.; Hunter, W. N.; Leonard, G. A.; Palou, J.; Walmsley, D.; Watt, C. I. F. J. Chem. Soc., Perkin Trans. 1 1993, 931-935.
83. (d) Kantrowski, E. J.; Kurth, M. J. Tetrahedron 2000, 56, 4317-4353.
84. Montalti, M.; Credi, A.; Prodi, L.; Gandolfi, M. T. Handbook of Photochemistry; CRC Taylor and Francis: Boca Raton, 2006.
85. Rehm, D.; Weller, A. Ber. Bunsen-Ges. Phys. Chem. 1969, 73, 834-839.
86. (a) Johnston, L. J.; Scaiano, J. C. Chem. Rev. 1989, 89, 521-547.
87. (b) Miranda, M. A.; Font-Sanchis, E.; Pérez-Prieto, J.; Scaiano, J. C. J. Org. Chem. 2001, 66, 2717-2721.
88. (c) Font-Sanchis, E.; Miranda, M. A.; Pérez-Prieto, J.; Scaiano, J. C. J. Org. Chem. 2002, 67, 6131-6135.
89. Samanta, A.; Ramachandram, B.; Saroja, G. J. Photochem. Photobiol. A: Chem. 1996, 101, 29-32.
90. Mella, M.; Freccero, M.; Albini, A. Tetrahedron 1996, 52, 5549-5562.
91. (a) Mella, M.; Freccero, M.; Albini, A. Tetrahedron 1996, 52, 5540-5562.
92. (b) Mella, M.; Freccero, M.; Soldi, T.; Fasani, E.; Albini, A. J. Org. Chem. 1996, 61, 1413-1422.
93. (c) Cardarelli, A. M.; Fagnoni, M.; Mella, M.; Albini, A. J. Org. Chem. 2001, 66, 7320-7327.
94. (a) Cabelli, D. E.; Bielski, B. H. J. J. Phys. Chem. 1983, 87, 1809-1812.
95. (b) von Sonntag, C. The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987.
96. (c) Cabelli, D. E. The Reactions of HO2/O2- Radicals in Aqueous Solution; Alfassi, Z. B., Ed.; Wiley: Chichester, 1997; pp 407.
97. (a) Oelgemöller, M.; Griesbeck, A. G.; Lex, J.; Haeuseler, A.; Schmittel, M.; Niki, M.; Hesek, D.; Inoue, Y. Org. Lett. 2001, 3, 1593-1596.
98. (b) Oelgemöller, M.; Haeuseler, A.; Schmittel, M.; Griesbeck, A. G.; Lex, J.; Inoue, Y. J. Chem. Soc., Perkin Trans. 2 2002, 676-686.
99. Gritzner, G.; Kuta, J. Pure Appl. Chem. 1984, 56, 461-466.
100. Matsubayashi, K.; Kubo, Y. J. Org. Chem. 2008, 73, 4915-4919.
101. (a) Zimmerman, H. E.; Amick, D. R. J. Am. Chem. Soc. 1973, 95, 3977-3982.
102. (b) Demuth, M.; Amrein, W.; Bender, C. O.; Braslavsky, S. E.; Burger, U.; George, M. V.; Lemmer, D.; Schaffner, K. Tetrahedron 1981, 37, 3245-3261.
103. (c) Schuster, D. I.; Calcaterra, L. T. J. Am. Chem. Soc. 1982, 104, 6397-6405.
104. (d) Sadler, D. E.; Wendler, J.; Olbrich, G.; Schaffner, K. J. Am. Chem. Soc. 1984, 106, 2064-2071.
105. (e) Wang, Z.; Weininger, S. J.; McGimpsey, W. G. J. Phys. Chem. 1993, 97, 374-378.
106. (f) Encinas, S.; Miranda, M. A.; Marconi, G.; Monti, S. Photochem. Photobiol. 1998, 67, 420-425.
107. (a) Bohne, C.; Kenedy, S. R.; Boch, R.; Negri, F.; Orlandi, G.; Siebrand, W.; Scaiano, J. C. J. Phys. Chem. 1991, 95, 10300-10306.
108. (b) Sakamoto, M.; Cai, X.; Hara, M.; Fujitsuka, M.; Majima, T. J. Am. Chem. Soc. 2004, 126, 9709-9714.
109. (c) Cai, X.; Sakamoto, M.; Fujitsuka, M.; Majima, T. Chem. Eur. J. 2005, 11, 6471-6477.
110. (d) Sakamoto, M.; Cai X.; Hara, M.; Fujitsuka, M.; Majima, T. J. Phys. Chem. A 2005, 109, 4657-4661.
111. Cai, X.; Sakamoto, M.; Hara, M.; Tojo, S.; Kawai, K.; Endo, M.; Fujitsuka, M.; Majima, T. J. Phys. Chem. A 2004, 108, 9361-9364.
112. Wagner, P. J. Acc. Chem. Res. 1971, 4, 168-177.
113. Yan, G.; Brinkmann, N. G.; Schaefer, H. F. III J. Phys. Chem. A 2003, 107, 9479-9485.