Stereoselective (2π + 2π) photocycloaddition of arylalkenes to chrysene

Chemistry Letters

Volumn , Issue 11, 2000, Pages 1238-1239

  Maeda, Hajime ^a   Waseda, Shigeyuki ^a   Mizuno, Kazuhiko ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034344658     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.1238     Document Type: Article

References (25)

1. a) A. Gilbert, in "Synthetic Organic Photochemistry," ed. by W. M. Horspool, Plenum Press, London (1984), p. 1.
2. b) J. J. McCullough, Chem. Rev., 87, 811 (1987).
3. c) R. A. Caldwell and D. Creed, Acc. Chem. Res., 13, 45 (1980).
4. a) K. Mizuno, R. A. Caldwell, A. Tachibana, and Y. Otsuji, Tetrahedron Lett., 33, 5779 (1992).
5. b) K. Mizuno, S. Konishi, T. Takata, and H. Inoue, Tetrahedron Lett., 37, 7775 (1996).
6. c) K. Mizuno, H. Maeda, Y. Inoue, A. Sugimoto, L. P. Vo, and R. A. Caldwell, Tetrahedron Lett., 41, 4913 (2000).
7. a) H. Karpf, O. E. Polansky, and M. Zander, Tetrahedron Lett., 1978, 339.
8. b) N. C. Yang, J. Masnovi, and W. Chiang, J. Am. Chem. Soc., 101, 6465 (1979).
9. c) N. C. Yang, J. Masnovi, W. -L. Chiang, T. Wang, H. Shou, and D. -D. H. Yang, Tetrahedron, 37, 3285 (1981).
10. d) R. Bunte, K. -D. Gundermann, J. Leitich, O. E. Polansky, and M. Zander, Chem. Ber., 119, 3521 (1986).
11. e) N. C. Yang, H. Can, S. S. Kim, J. M. Masnovi, P. W. Rafalko, E. F. Ezell, and G. R. Lenz, Tetrahedron Lett., 31, 3825 (1990).
12. Chrysene-sensitized photoreactions: a) D. I. Schuster and D. J. Blythin, J. Org. Chem., 35, 3190 (1970).
13. b) T. Arai, H. Sakuragi, and K. Tokumaru, Bull. Chem. Soc. Jpn., 55, 2204 (1982).
14. c) P. S. Engel, D. W. Horsey, D. E. Keys, C. J. Nalepa, and L. R. Soltero, J. Am. Chem. Soc., 105, 7108 (1983).
15. d) T. Karatsu, T. Hiresaki, T. Arai, H. Sakuragi, K. Tokumaru, and J. Wirz, Bull. Chem. Soc. Jpn., 64, 3355 (1991).
16. e) F. Elisei, G. G. Aloisi, L. Latterini, G. Galiazzo, and H. Görner, J. Chem. Soc., Faraday Trans., 91, 3117 (1995).
17. f) F. J. Steemers, H. G. Meuris, W. Verboom, D. N. Reinhoudt, E. B. van der Tol, and J. W. Verhoeven, J. Org. Chem., 62, 4229 (1997).
18. a) H. Karpf, O. E. Polansky, and M. Zander, Tetrahedron Lett., 1978, 2069.
19. b) H. Karpf, O. E. Polansky, and M. Zander, Monatsh. Chem., 112, 659 (1981).
20. c) L. D. Melikadze and E. G. Lekveishvili, Gazokondensaty Nefti, Mater. Sredneaziat. Nauch. Soveshch. Neftekhim. Khim. Pererab. Uglevodorodov, 2nd, 1967, 304; Chem. Abstr., 72, 3271m (1970).
21. c) L. D. Melikadze and E. G. Lekveishvili, Gazokondensaty Nefti, Mater. Sredneaziat. Nauch. Soveshch. Neftekhim. Khim. Pererab. Uglevodorodov, 2nd, 1967, 304; Chem. Abstr., 72, 3271m (1970).
22. Prolonged irradiation of 1a with α-cyanostilbene in benzene afforded (2π + 2π) photocycloadduct: R. A. Caldwell, personal communication.
23. 3), both in cyclohexane.
24. a) K. Mizuno and C. Pac, in "CRC Handbook of Organic Photochemistry and Photobiology," ed. by W. M. Horspool, P. -S. Song, CRC, London (1994), p. 358.
25. b) C. Pac, Pure Appl. Chem., 58, 1249 (1986).