Dihydrobenzofurans via dienone-phenol rearrangement of spirooxetanes from photoaddition of quinones with electron donor olefins

Heterocycles

Volumn 43, Issue 3, 1996, Pages 619-624

  Oshima, Takumi ^a   Nakajima, Yu Ichi ^a   Nagai, Toshikazu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011172747     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-7336     Document Type: Article

References (14)

1. a) K. Maruyama and A. Osuka, in The Chemistry of Quinonoid Compounds; ed. by S. Patai, Z. Rappoport, Wiley, New York, 1988, Part 2, p.759;
2. b) R. M. Wilson, S. W. Wunderly, T. F. Walsh, A. K. Musser, R. Outcalt, F. Geiser, S. K. Gee, W. Brabender, L. Jr. Yerino, T. T. Conrad, and G. A. Tharp, J. Am. Chem. Soc., 1982, 104, 4429;
3. c) K. Maruyama, T. Otsuki, and S. Tai, J. Org. Chem., 1985, 50, 52;
4. d) K. Maruyama and H. Imahori, J. Org. Chem., 1989, 54, 2692;
5. e) K. Maruyama and H. Imahori, J. Chem. Soc., Perkin Trans. 2, 1990, 257;
6. f) D. Bryce-Smith, E. H. Evans, A. Gilebert, and H. M. McNeil, J. Chem. Soc., Perkin Trans. 2, 1991, 1587;
7. g) D. Bryce-Smith, E. H. Evans, A. Gilbert, and H. M. McNeil, J. Chem. Soc., Perkin Trans. 2, 1992, 485.
8. N. J. Bunce and M. Hadley, Can. J. Chem., 1975, 53, 3240.
9. J.-H. Xu, L.-C. Wang, J.-W. Xu, B.-Z. Yan, and H.-C. Yuan, J. Chem, Soc., Perkin Trans, 1, 1994, 571.
10. a) J. March, in Advanced Organic Chemistry; Wiley, New York, 1992, p. 1079;
11. b) S. Chalais, P. Laszlo and A. Mathy, Tetrahedron Lett., 1986, 27, 2627.
12. S. H. Schroeter and C. M. Orlando, J. Org. Chem., 1969, 34, 1181.
13. For the crystal structure of similar spirooxetanes, see H. Tamura, T. Oshima, T. Nagai, A. Inaba, and H. Chihara, Acta Cryst., 1990, C46, 609.
14. T. Oshima and T. Nagai, Tetrahedron Lett., 1989, 30, 3443.