Photoinduced reactions of para-quinones with bicyclopropylidene leading to diverse polycyclic compounds with spirocyclopropanes

Journal of Organic Chemistry

Volumn 78, Issue 12, 2013, Pages 6211-6222

  Wang, Wei ^a   Zhang, Wen Jie ^a   Wang, Lei ^a   Quah, Ching Kheng ^b   Fun, Hoong Kun ^b,c   Xu, Jian Hua ^a   Zhang, Yan ^a  

^a NANJING UNIVERSITY   (China)

^b SCHOOL OF PHYSICS   (Malaysia)

^c KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

[No Author keywords available]

Indexed keywords

9 ,10-ANTHRAQUINONE; BICYCLOPROPYLIDENES; PHOTOCYCLOADDITION; PHOTOINDUCED REACTION; POLYCYCLIC COMPOUNDS; SPIROCYCLOPROPANES; SUBSTITUTION GROUPS; SYNTHETIC PROTOCOLS;

KETONES; OLEFINS;

PHOTOREACTIVITY;

ANTHRAQUINONE; BENZENE DERIVATIVE; BENZOQUINONE; CYCLOPROPANE DERIVATIVE; NAPHTHOQUINONE; POLYCYCLIC HYDROCARBON; QUINONE DERIVATIVE; SESQUITERPENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; IRRADIATION; LIGHT; MOLECULAR MECHANICS; PHOTOLYSIS; PHOTOREACTIVITY; SUBSTITUTION REACTION;

ANTHRAQUINONES; BENZOQUINONES; CYCLOADDITION REACTION; CYCLOPROPANES; LIGHT; MOLECULAR STRUCTURE; NAPHTHOQUINONES; PHOTOCHEMICAL PROCESSES; POLYCYCLIC COMPOUNDS; SPIRO COMPOUNDS;

EID: 84879390012     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4008767     Document Type: Article

References (91)

1. Bach, T.; Hehn, J. P. Angew. Chem., Int. Ed. 2011, 50, 1000-1045
2. Hoffmann, N. Chem. Rev. 2008, 108, 1052-1103
3. Griesbeck, A. G.; Hoffmann, N.; Warzecha, K.-D. Acc. Chem. Res. 2007, 40, 128-140
4. Hoffmann, N. Pure Appl. Chem. 2007, 79, 1949-1958
5. Yucel, B.; Valentic, N.; Noltemeyer, M.; de Meijere, A. Eur. J. Org. Chem. 2007, 4801-4090
6. Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020
7. Müller, F.; Mattay, J. Chem. Rev. 1993, 93, 99-117
8. Thibodeaux, C. J.; Chang, W.-C.; Liu, H.-W. Chem. Rev. 2012, 112, 1681-1709
9. Brackmann, F.; de Meijere, A. Chem. Rev. 2007, 107, 4493-4537
10. Chen, D. Y.-K.; Pouwer, R. H.; Richard, J.-A. Chem. Soc. Rev. 2012, 41, 4631-4642
11. Donaldson, W. A. Tetrahedron 2001, 57, 8589-8627
12. Carson, C. A.; Kerr, M. A. Chem. Soc. Rev. 2009, 38, 3051-3060
13. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117-3179
14. Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213-1269
15. Shi, M.; Shao, L.-X.; Lu, J.-M.; Wei, Y.; Mizuno, K.; Maeda, H. Chem. Rev. 2010, 110, 5883-5913
16. Ciufolini, M. A.; Rivera-Fortin, M. A.; Zuzukin, V.; Whitmire, K. H. J. Am. Chem. Soc. 1994, 116, 1272-1277
17. Ciufolini, M. A.; Rivera-Fortin, M. A.; Byrne, N. E. Tetrahedron Lett. 1993, 34, 3505-3508
18. de Meijere, A.; Schill, H.; Kozhushkov, S. I.; Walsh, R.; Müller, E. M.; Grubmüller, H. Russ. Chem. Bull. 2004, 53, 947-959
19. de Meijere, A.; von Seebach, M.; Zöllner, S.; Kozhushkov, S. I.; Belov, V. N.; Boese, R.; Haumann, T.; Benet-Buchholz, J.; Yufit, D. S.; Howard, J. A. K. Chem.-Eur. J. 2001, 7, 4021-4034
20. de Meijere, A.; Kozhushkov, S. I. Eur. J. Org. Chem. 2000, 3809-3822
21. de Meijere, A.; Kozhushkov, S. I.; Späth, T.; von Seebach, M.; Löhr, S.; Nüske, H.; Pohlmann, T.; Es-Sayed, M.; Bräse, S. Pure Appl. Chem. 2000, 72, 1745-1756
22. Traetteberg, M.; Simon, A.; Peters, E. M.; de Merjere, A. J. Mol. Struct. 1984, 118, 333-343
23. Boese, R.; Haumann, T.; Jemmis, E. D.; Kiran, B.; Kozhushkov, S. I.; de Meijere, A. Liebigs Ann. 1996, 913-919
24. Eckert-Maksić, M.; Maksić, Z. B.; Skancke, A.; Skancke, P. N. J. Phys. Chem. 1987, 91, 2786-2790
25. Hofland, A.; de Boer, T. J. Recl. Trav. Chim. Pays-Bas 1987, 106, 558-562
26. Gleiter, R.; Haider, R.; Conia, J. M.; Barnier, J. P.; de Meijere, A.; Weber, W. J. Chem. Soc., Chem. Commun. 1979, 130-132
27. Gleiter, R.; Spanget-Larson, J. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press, Ltd.: London, 1992; Vol. 2, pp 143-189.
28. Cordero, F. M.; Salvati, M.; Vurchio, C.; de Meijere, A.; Brandi, A. J. Org. Chem. 2009, 74, 4225-4231
29. Zanobini, A.; Brandi, A.; de Meijere, A. Eur. J. Org. Chem. 2006, 1251-1255
30. Zhao, L.-G.; de Meijere, A. Adv. Synth. Catal. 2006, 348, 2484-2492
31. Molchanov, A. P.; Diev, V. V.; Magull, J.; Vidović, D.; Kozhushkov, S. I.; de Meijere, A.; Kostikov, R. R. Eur. J. Org. Chem. 2005, 593-599
32. Schelper, M.; de Meijere, A. Eur. J. Org. Chem. 2005, 582-592
33. Yücel, B.; Arve, L.; de Meijere, A. Tetrahedron 2005, 61, 11355-11373
34. Hoyte, S. A.; Spencer, J. L. Organometallics 2011, 30, 5415-5423
35. Kozhushkov, S. I.; Yufit, D. S.; Ackermann, L. Org. Lett. 2008, 10, 3409-3412
36. Wu, D.-D.; Wang, L.; Xu, K.; Song, J.; Fun, H.-K.; Xu, J.-H.; Zhang, Y. Chem. Commun. 2012, 48, 1168-1170
37. Wu, D.-D.; He, M.-T.; Liu, Q.-D.; Wang, W.; Zhou, J.; Wang, L.; Fun, H.-K.; Xu, J.-H.; Zhang, Y. Org. Biomol. Chem. 2012, 10, 3626-3635
38. Wu, D.-D.; Huang, C.-M.; Wu, Y.-H.; H.-, K.; Xu, J.-H.; Zhang, Y. RSC Adv. 2013, 3, 7529-7536
39. Huang, C.-M.; Zheng, M.-M.; Xu, J.-H.; Zhang, Y. Molecules 2013, 18, 2942-2966
40. Gilbert, A. In CRC Handbook of Organic Photochemistry and Photobiology, 2 nd ed.; Horspool, W.; Lenci, F., Eds; CRC Press: Boca Raton, FL, 2004; pp 87/1-87/12.
41. Goerner, H. In CRC Handbook of Organic Photochemistry and Photobiology, 3 rd ed.; Griesbeck, A.; Oelgemoller, M.; Ghetti, F., Eds; CRC Press: Boca Raton, FL, 2012; Vol. 1, pp 683-714.
42. Maruyama, K.; Otsuki, T.; Tai, S. J. Org. Chem. 1985, 50, 52-60
43. Maruyama, K.; Imahori, H. J. Org. Chem. 1989, 54, 2692-2702
44. Eckert, G.; Goez, M. J. Am. Chem. Soc. 1994, 116, 11999-12009
45. Cleridou, S.; Covell, C.; Gadhia, A.; Gilbert, A.; Kamonnawin, P. Perkin 1 2000, 1149-1155
46. Bosch, E.; Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 386-395
47. Kokubo, K.; Masaki, T.; Oshima, T. Org. Lett. 2000, 2, 1979-1981
48. Xue, J.; Xu, J.-W.; Yang, L.; Xu, J.-H. J. Org. Chem. 2000, 65, 30-40
49. Xu, J.-H.; Song, Y.-L.; Zhang, Z.-G.; Wang, L.-C.; Xu, J.-W. Tetrahedron 1994, 50, 1199-1210
50. Xu, J.-H.; Wang, L.-C.; Xu, J.-W.; Yan, B.-Z.; Yuan, H.-C. J. Chem. Soc., Perkin Trans. 1 1994, 571-577
51. Miyashi, T.; Konno, A.; Takahashi, Y.; Kanecko, A.; Suzuki, T.; Mukai, T.; Koga, N.; Iwamura, H. Tetrahedron Lett. 1989, 30, 5297-5300
52. Christl, M.; Braun, M.; Deeg, O.; Wolff, S. Eur. J. Org. Chem. 2011, 968-982
53. Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259-271
54. Bunce, N. J.; Hadley, M. Can. J. Chem. 1975, 53, 3240-3246
55. Haga, N.; Takayanagi, H.; Tokumaru, K. J. Chem. Soc., Perkin Trans. 2 2002, 734-745
56. Kuboyama, A. Bull. Chem. Soc. Jpn. 1978, 51, 2771-2775
57. Abe, M. In Handbook of Synthetic Photochemistry; Albini, A.; Fagnoni, M., Eds.; Wiley-VCH: Weinheim, 2009; pp 217-239.
58. Griesbeck, A. G.; Fiege, M. In Molecular and Supramolecular Photochemistry; Ramamurthy, V.; Schanze, K. S., Eds.; Marcel Dekker: New York, 2000; Vol. 6, pp 33-100.
59. Fleming, S. A.; Bradford, C. L.; Gao, J. J. In Molecular and Supramolecular Photochemistry; Ramamurthy, V.; Schanze, K. S., Eds.; Marcel Dekker: New York, 1997; Vol. 1, pp 187-243.
60. Bach, T. Synthesis 1998, 683-703
61. Jones, G. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1981; Vol. 5, pp 1-122.
62. Herre, W.; Weis, P. Spectrochim. Acta, Part A 1973, 29, 203-205
63. Kemp, D. R.; Porter, G. Proc. R. Soc. London, Ser. A 1971, 326, 117-130
64. Ogino, K.; Minami, T.; Kozuka, S.; Kinoshita, T. J. Org. Chem. 1980, 45, 4694-4698
65. Marshall, J. A.; Brady, S. F.; Andersen, N. H. Fortschr. Chem. Org. Naturst. 1974, 31, 283-376
66. Daniel, M.; Purkayastha, R. P. In Handbook of Phetoalexin Metablism and Action; Marcel Dekker: New York, 1995.
67. Afzal, M.; Al Oriquat, G. Heterocycles 1986, 24, 2943-2961
68. Iwata, C.; Miyashita, K.; Imao, T.; Masuda, K.; Kondo, N.; Uchida, S. Chem. Pharm. Bull. 1985, 33, 853-855
69. Fivush, A. M.; Strunk, S. R. Synth. Commun. 1996, 26, 1623-1627
70. Swenton, J. S.; Callinan, A.; Wang, S. P. J. Org. Chem. 1992, 57, 78-85
71. Swenton, J. S.; Bradin, D.; Gates, B. D. J. Org. Chem. 1991, 56, 6156-6163
72. Iwata, C.; Yamada, M.; Ida, Y.; Imao, T.; Miyagawa, H.; Miyashita, K. Chem. Pharm. Bull. 1988, 36, 2864-2871
73. Iwata, C.; Yamada, M.; Shinoo, Y.; Kobayashi, K.; Okada, H. Chem. Pharm. Bull. 1980, 28, 1932-1934
74. Iwata, C.; Yamada, M.; Shinoo, Y.; Kobayashi, K.; Okada, H. J. Chem. Soc., Chem. Commun. 1977, 888-889
75. Otsuki, T. Bull. Chem. Soc. Jpn. 1976, 2596-2605
76. Bryce-Smith, D.; Evans, E. H.; Gilbert, A.; McNeill, H. S. J. Chem. Soc., Perkin Trans. 1 1992, 485-489
77. Ochiai, M.; Arimoto, M.; Fujita, E. J. Chem. Soc. Chem. Commun. 1981, 460-461
78. Liu, H.-J.; Chan, W. H. Can. J. Chem. 1980, 58, 2196-2198
79. Maruyama, K.; Tai, S. Chem. Lett. 1985, 681-684
80. Maruyama, K.; Narita, N. Bull. Chem. Soc. Jpn. 1980, 53, 757-763
81. Naito, T.; Makita, Y.; Yazaki, S.; Kaneko, C. Chem. Pharm. Bull. 1986, 34, 1505-1517
82. Burger, U.; Lottaz, P.-A.; Millasson, P.; Bernardinelli, G. Helv. Chim. Acta 1994, 77, 850-858
83. Maruyama, K.; Imahori, H. J. Chem. Soc., Perkin Trans. 2 1990, 257-265
84. Li, X. M.; Wang, L.; Xu, J. H.; Zhang, S. S.; Fun, H.-K. Acta Crystallogr., Sect. E: Struct. Rep. Online 2003, E59, o1742-ol744
85. Kuboyama, A. Bull. Chem. Soc. Jpn. 1960, 33, 1027-1030
86. Stevenson, P. E. J. Mol. Spectrosc. 1965, 17, 58-85
87. Yoshihara, T.; Yamaji, M.; Itoh, T.; Nishimura, J.; Shizuka, H.; Tobita, S. J. Photochem. Photobiol., A 2001, 140, 7-13
88. Lamola, A. A.; Hammond, G. S. J. Chem. Phys. 1965, 43, 2129-2135
89. Zander, M. Ber. Bunsen-Ges. 1967, 71, 424-429
90. Griesbeck, A. G.; Abe, M.; Bondock, S. Acc. Chem. Res. 2004, 37, 919-928
91. Griesbeck, A. G.; Mauder, H.; Stadtmüller, S. Acc. Chem. Res. 1994, 27, 70-75