Diels-Alder adducts of of ortho-benzoquinones: Rearrangements and further transformations

Canadian Journal of Chemistry

Volumn 75, Issue 6, 1997, Pages 805-816

  Carlini, Rina ^a   Higgs, Kerianne ^a   Taylor, Nicholas ^a   Rodrigo, Russell ^b  

^a UNIVERSITY OF WATERLOO   (Canada)

^b WILFRID LAURIER UNIVERSITY   (Canada)

Author keywords

Benzoquinone; Diels Alder; Phenanthraquinone; Phenanthrofuran; Rearrangement

Indexed keywords

ALCOHOLS; AROMATIC COMPOUNDS; ELECTRON TRANSPORT PROPERTIES; OXIDATION;

ELECTRON-WITHDRAWING GROUPS; QUINONES;

ADDITION REACTIONS;

EID: 0031163783     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v97-097     Document Type: Article

References (20)

1. (a) P. Deslongchamps. Pure Appl. Chem. 49, 1329 (1977);
2. (b) A.C. Bazan, J.H. Edwards, and U. Weiss. Tetrahedron Lett. 147 (1977);
3. (c) S. Yamamura, Y. Shizuri, H. Shigemori, Y. Okhuno, and M. Okhubo. Tetrahedron, 47, 635 (1991).
4. R. Carlini, C-L. Fang, D. Herrington, K. Higgs, R. Rodrigo, and N. Taylor. Aust. J. Chem. 50, 271 (1997).
5. T.H. Lee, C.-C. Liao, and N.-C. Liu. Tetrahedron Lett. 37, 5897 (1996).
6. S. Inayama and Y. Yanagita. J. Org. Chem. 27, 1465 (1962).
7. A. Planas, J. Tomas, and J.-J. Bonet. Tetrahedron Lett. 28, 471 (1987).
8. (a) F.B.H. Ahmad, J.M. Bruce, J. Khalafy, V. Pejanovic, K. Sabetian, and I. Watt. J. Chem. Soc. Chem. Commum. 166 (1981);
9. (b) F.B.H. Ahmad, J.M. Bruce, J. Khalafy, and K. Sabetian. J. Chem. Soc. Chem. Commun. 169 (1981);
10. (c) M.U. Akpuaka, R.L. Beddoes, J.M. Bruce. S. Fitzjohn, and O. Mills. J. Chem. Soc. Chem. Commun. 686 (1982).
11. S.C. Cooper and P.G. Sammes. J. Chem. Soc. Chem. Commun. 633 (1980).
12. (a) G. Vidari, S. Ferrino, and P.A. Grieco. J. Am. Chem. Soc. 106, 3539 (1984);
13. (b) T.R. Hoye, A.S. Magee, and W.S. Trumper. Synth. Commun. 12, 183 (1987);
14. (c) K. Mori. Tetrahedron, 30, 3807 (1974);
15. (d) R.K. Boeckmann and D.M. Demko. J. Org. Chem. 47, 1789 (1982).
16. L. Shide, R. Mayer, and G. Rucker. Planta Med. 53, 332 (1987).
17. J.M. Bruce. J. Chem. Soc. 360 (1960).
18. R. Al-Hamdany and S. Salih. J. Iraqi Chem. Soc. 6-7, 61 (1982); Chem. Abstr. 101, 210214c (1984).
19. R. Al-Hamdany and S. Salih. J. Iraqi Chem. Soc. 6-7, 61 (1982); Chem. Abstr. 101, 210214c (1984).
20. R.C. Cookson, T.A. Crabb, J.J. Frankel, and J. Hudec. Tetrahedron, Suppl. 7, 355 (1966).