A novel photorearrangement of aryl naphthylmethyl ethers. Formation of cyclohexa-2,4-dienone derivatives

Tetrahedron Letters

Volumn 39, Issue 26, 1998, Pages 4683-4686

  Yoshimi, Yasuharu ^a   Sugimoto, Akira ^a   Maeda, Hajime ^a   Mizuno, Kazuhiko ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE;

ARTICLE; IRRADIATION; JAPAN; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0032565938     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00877-6     Document Type: Article

References (18)

1. 1. Kharasch, M. S.; Stampa, G.; Nudenberg, W. Science 1952, 116, 309; Kelly, D. P.; Pinhey, J. T.; Rigby, R. D. G. Tetrahedron Lett. 1966, 48, 5953-5956.
2. 1. Kharasch, M. S.; Stampa, G.; Nudenberg, W. Science 1952, 116, 309; Kelly, D. P.; Pinhey, J. T.; Rigby, R. D. G. Tetrahedron Lett. 1966, 48, 5953-5956.
3. 2. Singh, V.; Porinchu, M. Tetrahedron Lett. 1993, 34, 2817-2820; Barton, D. H. R.; Chung, S. K.; Kwon, T. W. Tetrahedron Lett. 1996, 37, 3631-3634; Carlini, R.; Higgs, K.; Rodrigo, R.; Taylor, N. J. Chem. Soc., Chem. Commun. 1998, 65-66; Polisetti, D. R.; Chien-Hsing, C.; Chun-Chen, L. J. Chem. Soc., Chem. Commun. 1998, 155-156.
4. 2. Singh, V.; Porinchu, M. Tetrahedron Lett. 1993, 34, 2817-2820; Barton, D. H. R.; Chung, S. K.; Kwon, T. W. Tetrahedron Lett. 1996, 37, 3631-3634; Carlini, R.; Higgs, K.; Rodrigo, R.; Taylor, N. J. Chem. Soc., Chem. Commun. 1998, 65-66; Polisetti, D. R.; Chien-Hsing, C.; Chun-Chen, L. J. Chem. Soc., Chem. Commun. 1998, 155-156.
5. 2. Singh, V.; Porinchu, M. Tetrahedron Lett. 1993, 34, 2817-2820; Barton, D. H. R.; Chung, S. K.; Kwon, T. W. Tetrahedron Lett. 1996, 37, 3631-3634; Carlini, R.; Higgs, K.; Rodrigo, R.; Taylor, N. J. Chem. Soc., Chem. Commun. 1998, 65-66; Polisetti, D. R.; Chien-Hsing, C.; Chun-Chen, L. J. Chem. Soc., Chem. Commun. 1998, 155-156.
6. 2. Singh, V.; Porinchu, M. Tetrahedron Lett. 1993, 34, 2817-2820; Barton, D. H. R.; Chung, S. K.; Kwon, T. W. Tetrahedron Lett. 1996, 37, 3631-3634; Carlini, R.; Higgs, K.; Rodrigo, R.; Taylor, N. J. Chem. Soc., Chem. Commun. 1998, 65-66; Polisetti, D. R.; Chien-Hsing, C.; Chun-Chen, L. J. Chem. Soc., Chem. Commun. 1998, 155-156.
7. 3. Jung, Y. S.; Mariano, P. S. Tetrahedron Lett. 1993, 34, 4611-4614; Hasegawa, E.; Tamura, Y.; Horaguchi, T.; Isogai, K.; Suzuki, T. Tetrahedron Lett. 1994, 35, 8642-8646; Schultz, A. G.; Antoulinakis, G. E. J. Org. Chem. 1996, 61, 4555-4559.
8. 3. Jung, Y. S.; Mariano, P. S. Tetrahedron Lett. 1993, 34, 4611-4614; Hasegawa, E.; Tamura, Y.; Horaguchi, T.; Isogai, K.; Suzuki, T. Tetrahedron Lett. 1994, 35, 8642-8646; Schultz, A. G.; Antoulinakis, G. E. J. Org. Chem. 1996, 61, 4555-4559.
9. 3. Jung, Y. S.; Mariano, P. S. Tetrahedron Lett. 1993, 34, 4611-4614; Hasegawa, E.; Tamura, Y.; Horaguchi, T.; Isogai, K.; Suzuki, T. Tetrahedron Lett. 1994, 35, 8642-8646; Schultz, A. G.; Antoulinakis, G. E. J. Org. Chem. 1996, 61, 4555-4559.
10. 4. Gerhard, Q. Angew. Chem., Int. Ed. Engl. 1972, 11, 1072-1087.
11. 5. Schuster, D. I. Acc.Chem. Res. 1978, 11, 65-73; Schultz, A. G. Acc. Chem. Res. 1990, 23, 207-213.
12. 5. Schuster, D. I. Acc.Chem. Res. 1978, 11, 65-73; Schultz, A. G. Acc. Chem. Res. 1990, 23, 207-213.
13. +).
14. 7. Thermal reactions of 2a,b were carried out with out solvent under degassed conditions at 250°C for 1h.
15. 8. Phenol-catalyzed rearrangement of 2a,b to 3a,b did not proceed in the dark. Therefore, phenol derivatives in the present photoreactions should be indispensable for the secondary photorearrangement.
16. 9. Murov, S. L.; Carmichael, I.; Hug, G. L. "Handbook of Photochemistry ", Marcel Dekker Inc. New York, p. 17 and p. 76 (1993).
17. 10. In general, the photo-Claisen rearrangement is started by the direct excitation of the phenoxy group.
18. 11. Photocleavage reaction via photoinduced electron transfer: Saeva, F. D. In Photoinduced Electron Transfer I , Mattay, J., Ed.; Springer-Verlag: Berlin, 1990, pp. 59-92.