Geometrically specific hydrogen transfer in the reaction of terminally alkyl-substituted 1,3-dienes with 1,4-quinones

Australian Journal of Chemistry

Volumn 53, Issue 2, 2000, Pages 109-121

  Cameron, Donald W ^a   Heisey, Ross M ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

Cycloaddition; Dienes; Hydrogen transfer; Quinones

Indexed keywords

EID: 0043229518     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/ch00027     Document Type: Article

References (35)

1. Roush, W.R., and Barda, D. A., J. Am. Chem. Soc., 1997, 119, 7402.
2. Kienzle, F., Mergelsberg, I., Stadlwieser, J., and Arnold, W., Helv. Chim. Acta, 1985, 68, 1133.
3. Cameron, D. W., Feutrill, G. I., Heisey, R. M., and Teo, A. A. L., unpublished data.
4. Chretien-Bessiere, Y., and Leotte, H., C. R. Seances Acad. Sci., 1962, 255, 723.
5. Cazeau, P., Duboudin, F., Moulines, F., Babot, O., and Dunogues, J., Tetrahedron. 1987, 43, 2089.
6. Piers, E., and Phillips-Johnson, W. M., Can. J. Chem., 1975, 53, 1281.
7. Bohlmann, F., and Zdero, C., Chem. Ber., 1973, 106, 3779.
8. Akita, T., Yakugaku Zasshi, 1962, 82, 91
9. (Chem. Abstr., 1962, 57, 9711c).
10. Spangler, C. W., McCoy, R. K., and Karavakis, A. A., J. Chem. Soc., Perkin Trans. 1, 1986, 1203.
11. Ansell, M. F., and Bignold, A. J., J. Chem. Soc., Chem. Commun., 1969, 1096.
12. Mikolajczak, K. L., and Smith, C. R., J. Org. Chem., 1978, 43, 4762.
13. Ireland, R. E., Mueller, R. H., and Wiliard, A. K., J. Am. Chem. Soc., 1976, 98, 2868.
14. Ireland, R. E., Wipf, P., and Armstrong, J. D., J. Org. Chem., 1991, 56, 650.
15. Rappe, C., and Adestrom, R., Acta Chem. Scand., 1965, 19, 383.
16. Cameron, D. W., Looney, M. G., and Pattermann, J. A., Tetrahedron Lett., 1995, 36, 7555.
17. Kende, A. S., and Toder, B. H., J. Org. Chem., 1982, 47, 163.
18. Cardellach, J., Estopa, C., Font, J., Moreno-Manas, M., Ortuno, R. M., Sanchez-Ferrando, F., Valle, S., and Vilamajo, L., Tetrahedron, 1982, 38, 2394.
19. Cameron, D. W., Crosby, I. T., and Feutrill, G. I., Tetrahedron Lett., 1992, 33, 2855.
20. Fujimoto, Y., Kihara, T., Isono, K., Tsunoda, H., Tatsuno, T., Matsumoto, K., and Hirokawa, H., Chem. Pharm. Bull., 1984, 32, 1583;
21. Lewis, F. D., Howard, D. K., Barancyk, S. V., and Oxman, J. D., J. Am. Chem. Soc., 1986, 108, 3016.
22. Banville, J., and Brassard, P., J. Chem. Soc., Perkin Trans, 1, 1976, 1852.
23. Hoffman, R. V., and Kim, H.-O., J. Org. Chem., 1991, 56, 1014.
24. Aumuller, A., and Hunig, S., Liebigs Ann. Chem., 1986, 165.
25. Guerriero, A., D'Ambrosio, M., Cuomo, V., Vanzanella, F., and Pietra, F., Helv. Chim. Acta, 1989, 72, 438.
26. Lozanova, A. V., Moiseenkov, A. M., and Semenovskii, A. V., Izv. Akad. Nauk SSSR, Ser. Khim., 1980, 1932;
27. Struchkova, M. I., Lozanova, A. V., Moiseenkov, A. M., and Semenovskii, A. V., Izv. Akad. Nauk SSSR. Ser. Khim., 1980, 2655.
28. Camps, F., Coll, J., and Guitart, J., Tetrahedron, 1987, 43, 2329.
29. Jackman, L. M., and Wiley, R. H., J. Chem. Soc., 1960, 2881.
30. Chuman, T., and Noguchi, M., Tetrahedron Lett., 1977, 18, 3045.
31. Josey, A. D., Angew. Chem., Int. Ed. Engl, 1981, 20, 686.
32. Drexler, J., Lindermayer, R., Hassan, M. A., and Sauer, J., Tetrahedron Lett., 1985, 26, 2555;
33. Drexler, J., Lindermayer, R., Hassan, M. A., and Sauer, J., Tetrahedron Lett., 1985, 26, 2559.
34. Arbuzova, I. A., and Nikolyan, V. N., Zh. Org. Khim., 1969, 5, 2125.
35. Rogan, J. B., J. Org. Chem., 1962, 27, 3910.