Photochemical preparation of highly functionalized 1-indanones

Journal of Organic Chemistry

Volumn 69, Issue 22, 2004, Pages 7582-7591

  Wessig, Pablo ^a   Glombitza, Clemens ^a   Müller, Gunnar ^a   Teubner, Janek ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

IRRADIATION; PHOTOCHEMICAL REACTIONS; QUANTUM THEORY; SYNTHESIS (CHEMICAL);

CARBONYL GROUPS; QUANTUM CHEMICALS;

ORGANIC COMPOUNDS;

1 INDANONE DERIVATIVE; CARBONYL DERIVATIVE; INDANONE DERIVATIVE; KETONE; OXYGEN; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CYCLIZATION; IRRADIATION; PHOTOCHEMISTRY; QUANTUM CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 6344280673     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040173x     Document Type: Article

References (64)

1. (a) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168.
2. (b) Wagner, P. J. Top. Curr. Chem. 1876, 66, 1.
3. (c) Wagner, P. J. Acc. Chem. Res. 1989, 22, 83.
4. (d) Wagner, P. J., Park, B.-S. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker Inc.: New York, 1991; p 227.
5. (e) Wagner, P. J. In CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed.; Horspool, W. M., Lenci, F., Eds.; CRC Press: Boca Raton, FL, 2003; p 58-1.
6. Wessig, P. In CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed.; Horspool, W. M., Lenci, F. Eds.; CRC Press: Boca Raton, FL, 2003; p 57-1.
7. (a) Wessig, P.; Schwarz, J.; Lindemann, U.; Holthausen, M. C. Synthesis 2001, 1258.
8. (b) Wessig, P.; Mühling, O. Angew. Chem., Int. Ed. 2001, 40, 1064.
9. (c) Wessig, P.; Mühling, O. Helv. Chim. Acta 2003, 86, 865.
10. (a) McMorris, T. C.; Voeller, B. Photochemistry 1971, 10, 3253.
11. (b) Fukuoka, M.; Kuroyanagi, M.; Yoshishira, K.; Natori, S. Chem. Pharm. Bull 1978, 26, 2365.
12. (c) Bardouille, V.; Mootoo, B. S.; Hirotsu, K.; Clardy, J. Phytochemistry 1978, 17, 275.
13. (d) Evans, I. A. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; American Chemical Society: Washington, DC, 1984; Vol. 2, Section 1171.
14. (a) Bergmark, W. R. J. Chem. Soc., Chem. Commun. 1978, 61.
15. (b) Bergmark, W. R.; Barnes, C.; Clark, J.; Paparian, S.; Marynowski, S. J. Org. Chem. 1985, 50, 5612.
16. Netto-Ferreira, J. C.; Scaiano, J. C. J. Am. Chem. Soc. 1891, 113, 5800.
17. Klán, P.; Miroslav, Z.; Heger, D. Org. Lett. 2000, 2, 1569.
18. Pelliccioli, A. P.; Klán, P.; Zabadal, M.; Wirz, J. J. Am. Chem. Soc. 2001, 123, 7931.
19. (a) Koser, G. F.; Relenyi, A. G.; Kalos, A. N.; Rebrovic, L.; Wettach, R. H. J. Org. Chem. 1982, 47, 2487.
20. (b) Lodaya, J. S.; Koser, G. F., J. Org. Chem. 1888, 52, 210.
21. (a) Deuchert, K.; Hertenstein, U.; Hünig, S.; Wehner, G. Chem. Ber. 1979, 112, 2045.
22. (b) Hünig, S.; Marschner, C. Chem. Ber. 1989, 122, 1329.
23. (c) Hünig, S.; Wehner, G. Synthesis 1975, 180.
24. (a) Rieke, R. D.; Hundall, P. M. J. Am. Chem. Soc. 1972, 94, 7178.
25. (b) Rieke, R. D.; Bales, S. E. J. Am. Chem. Soc. 1874, 96, 1775.
26. This behavior was already observed previously: see ref 3c.
27. Horio, Y.; Torisawa, Y.; Ikegami, S. Chem. Pharm. Bull. 1985, 33, 5562.
28. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
29. (b) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, L, Pattenden, G., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 3, pp 521-549.
30. Mizushima, E.; Sato, K; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563.
31. (a) Unger, F. Liebigs Ann. 1933, 504, 267.
32. (b) Price, C. C.; Lewis, F. M. J. Am. Chem. Soc. 1939, 61, 2553.
33. (c) House, H. O.; Paragamian, V.; Ro, R. S.; Wluka, D. J. J. Am. Chem. Soc. 1960, 82, 1452.
34. (a) Pletnev, A. A.; Larock, R. C. J. Org. Chem. 2002, 67, 9428.
35. (b) Pletnev, A. A.; Larock, R. C. Tetrahedron Lett. 2002, 43, 2133.
36. (a) Dieckmann, W. Chem. Ber. 1922, 55, 2470.
37. (b) Titley, A. F. J. Chem. Soc. 1928, 2571.
38. (c) Ghosal, M.; Karpha, T. K.; Pal, S. K.; Mukherjee, D. Tetrahedron Lett. 1995, 36, 2527.
39. Keumi, T.; Matsuura, K.; Nakayama, N.; Tsubota, T.; Morita, T. Tetrahedron 1993, 49, 537.
40. Brunette, S. R.; Lipton, M. A. J. Org. Chem. 2000, 65, 5114.
41. (a) Nikolaev, V. A.; Popik, V. V. Tetrahedron Lett. 1992, 33, 4483.
42. (b) Ceccherelli, P.; Curini, M.; Marcotullio, M. C.; Rosati, O.; Wenkert, E. J. Org. Chem. 1990, 55, 311.
43. (a) Bishop, R.; Hamer, N. K. J. Chem. Soc. 1970, 1193.
44. (b) Maruyama, K.; Ono, K.; Osugi, J. Bull. Chem. Soc. Jpn. 1972, 45, 847.
45. (c) Kopecky, K. R.; Filby, J. E. Can. J. Chem. 1979, 57, 283.
46. (d) Wagner, P. J.; Park, B.; Sobczak, M.; Frey, J.; Rappoport, Z. J. Am. Chem. Soc. 1995, 777, 7619.
47. Smith, A. B.; Agosta, W. C. J. Am. Chem. Soc. 1973, 95, 1961.
48. (a) Rao, V. B.; Wolff, S.; Agosta, W. C. J. Am. Chem. Soc. 1985, 107, 521.
49. (b) Agosta, W. C.; Caldwell, R. A.; Jay, J.; Johnston, L. J.; Venepalli, B. R.; Scaiano, J. C.; Singh, M.; Wolff, S. J. Am. Chem. Soc. 1987, 109, 3050.
50. Negishi, E.; Coperet, C.; Ma, S.; Mita, T.; Sugihara, T.; Tour, J. M. J. Am. Chem. Soc. 1996, 118, 5904.
51. Dugan, J. J.; deMayo, P.; Nisbet, M.; Robinson, J. R.; Anchel, M. J. Am. Chem. Soc. 1966, 88, 2838.
52. Kerfanto, M.; Quentin, J. P.; Raphalen, D.; Véne, J. Bull. Soc. Chim. Fr. 1968, 4526.
53. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Gui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.9; Gaussian, Inc., Pittsburgh PA, 1998.
54. B3PW91 is Becke's 3-parameter functional (Becke, A. D. J. Chem. Phys. 1993, 98, 5648), with the nonlocal correlation provided by the Perdew 91 expression (Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R.; Singh, D. J.; Fiolhais, C. Phys. Rev. B 1992, 46).
55. B3PW91 is Becke's 3-parameter functional (Becke, A. D. J. Chem. Phys. 1993, 98, 5648), with the nonlocal correlation provided by the Perdew 91 expression (Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R.; Singh, D. J.; Fiolhais, C. Phys. Rev. B 1992, 46).
56. Reimann, E.; Renz, H. Arch. Pharm. 1993, 326, 253.
57. (a) Gebicki, J.; Krantz, A. J. Chem. Soc., Perkin Trans. 2 1984, 1623.
58. (b) Wagner, P. J.; Subrahmanyam, D.; Park, B. J. Am.Chem. Soc. 1991, 113, 709.
59. (c) Marcinek, A.; Michalak, J.; Rogowski, J.; Tang, W.; Bally, T.; Gebicki, J. J. Chem. Soc., Perkin Trans. 2 1992, 1353.
60. (a) Pan, K.; Ho, T. J. Chin. Chem. Soc. (Taipei) 1997, 44, 243.
61. (b) O-kawa, K.; Nakamura, Y.; Nishimura, J. Tetrahedron Lett. 2000, 41, 3103.
62. (c) Nicolaou, K. C.; Gray, D.; Tae, J. Angew. Chem., Int. Ed. 2001, 40, 3675.
63. (d) Nakamura, Y.; O-kawa, K.; Minami, S.; Ogawa, T.; Tobita, S.; Nishimura, J. J. Org. Chem. 2002, 67, 1247.
64. (e) Nicolaou, K. C.; Gray, D.; Tae, J. J. Am. Chem. Soc. 2004, 126, 613.