Lewis Acid-Directed Reactions of Quinones with Styrenyl Systems: The Case of 2-Methoxy-3-methyl-1,4-benzoquinone

Journal of Organic Chemistry

Volumn 63, Issue 6, 1998, Pages 1929-1934

  Engler, Thomas A ^a   Iyengar, Rajesh ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001667158     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971937u     Document Type: Article

References (27)

1. (a) Engler, T. A.; Combrink, K. D.; Ray, J. E. J. Am. Chem. Soc. 1988, 110, 7931-7933.
2. (b) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O., Jr.; Ray, J. E. J. Org. Chem. 1994, 59, 6567-6587.
3. (c) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588-6599.
4. Engler, T. A.; Chai, W.; LaTessa, K. O. J. Org. Chem. 1996, 61, 9297-9308.
5. (e) Engler, T. A.; Meduna, S. P.; LaTessa, K. O.; Chai, W. J. Org. Chem. 1996, 61, 8598-8603.
6. (f) Engler, T. A.; Gfesser, G. A.; Draney, B. W. J. Org. Chem. 1995, 60, 3700-3706.
7. (a) Tou, J. S.; Reusch, W. J. Org. Chem. 1980, 45, 5012-5014.
8. For seminal studies on the importance of the site of Lewis acid coordination to quinones in Diels-Alder reactions, see: (b) Dickinson, R. A.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. (c) Stojanac, Z.; Dickinson, R. A.; Stojanac, N.; Woznow, R. J.; Valenta, Z. Ibid. 1975, 53, 616-618. (d) Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. For studies with other 2-methoxy-1,4-benzoquinones, see: (e) Hendrickson, J. B.; Singh, V. J. Chem. Soc., Chem. Commun. 1983, 837-838. (f) Hendrickson, J. B.; Haestier, A. M.; Stieglitz, S. G.; Foxman, B. M. New. J. Chem. 1990, 14, 689-693. (g) Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
9. For seminal studies on the importance of the site of Lewis acid coordination to quinones in Diels-Alder reactions, see: (b) Dickinson, R. A.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. (c) Stojanac, Z.; Dickinson, R. A.; Stojanac, N.; Woznow, R. J.; Valenta, Z. Ibid. 1975, 53, 616-618. (d) Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. For studies with other 2-methoxy-1,4-benzoquinones, see: (e) Hendrickson, J. B.; Singh, V. J. Chem. Soc., Chem. Commun. 1983, 837-838. (f) Hendrickson, J. B.; Haestier, A. M.; Stieglitz, S. G.; Foxman, B. M. New. J. Chem. 1990, 14, 689-693. (g) Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
10. For seminal studies on the importance of the site of Lewis acid coordination to quinones in Diels-Alder reactions, see: (b) Dickinson, R. A.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. (c) Stojanac, Z.; Dickinson, R. A.; Stojanac, N.; Woznow, R. J.; Valenta, Z. Ibid. 1975, 53, 616-618. (d) Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. For studies with other 2-methoxy-1,4-benzoquinones, see: (e) Hendrickson, J. B.; Singh, V. J. Chem. Soc., Chem. Commun. 1983, 837-838. (f) Hendrickson, J. B.; Haestier, A. M.; Stieglitz, S. G.; Foxman, B. M. New. J. Chem. 1990, 14, 689-693. (g) Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
11. For seminal studies on the importance of the site of Lewis acid coordination to quinones in Diels-Alder reactions, see: (b) Dickinson, R. A.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. (c) Stojanac, Z.; Dickinson, R. A.; Stojanac, N.; Woznow, R. J.; Valenta, Z. Ibid. 1975, 53, 616-618. (d) Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. For studies with other 2-methoxy-1,4-benzoquinones, see: (e) Hendrickson, J. B.; Singh, V. J. Chem. Soc., Chem. Commun. 1983, 837-838. (f) Hendrickson, J. B.; Haestier, A. M.; Stieglitz, S. G.; Foxman, B. M. New. J. Chem. 1990, 14, 689-693. (g) Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
12. For seminal studies on the importance of the site of Lewis acid coordination to quinones in Diels-Alder reactions, see: (b) Dickinson, R. A.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. (c) Stojanac, Z.; Dickinson, R. A.; Stojanac, N.; Woznow, R. J.; Valenta, Z. Ibid. 1975, 53, 616-618. (d) Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. For studies with other 2-methoxy-1,4-benzoquinones, see: (e) Hendrickson, J. B.; Singh, V. J. Chem. Soc., Chem. Commun. 1983, 837-838. (f) Hendrickson, J. B.; Haestier, A. M.; Stieglitz, S. G.; Foxman, B. M. New. J. Chem. 1990, 14, 689-693. (g) Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
13. For seminal studies on the importance of the site of Lewis acid coordination to quinones in Diels-Alder reactions, see: (b) Dickinson, R. A.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1972, 50, 2377-2380. (c) Stojanac, Z.; Dickinson, R. A.; Stojanac, N.; Woznow, R. J.; Valenta, Z. Ibid. 1975, 53, 616-618. (d) Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can J. Chem. 1979, 57, 3308-3319. For studies with other 2-methoxy-1,4-benzoquinones, see: (e) Hendrickson, J. B.; Singh, V. J. Chem. Soc., Chem. Commun. 1983, 837-838. (f) Hendrickson, J. B.; Haestier, A. M.; Stieglitz, S. G.; Foxman, B. M. New. J. Chem. 1990, 14, 689-693. (g) Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
14. Mandell, L.; Roberts, E. C. J. Heterocycl. Chem. 1965, 2(4), 479-480 and references therein.
15. 4 produced unusual 2:1 propenylbenzene-quinone adducts; see ref 7.
16. (b) The structures of these products also support the 5 + 2 cycloaddition mechanism.
17. (a) Turin, E.; Nielson, R. M.; Merbach, A. E. Inorg. Chim. Acta 1987, 134, 79-85, 67-78.
18. (b) Bachand, B.; Wuest, J. D. Organometallics 1991, 10, 2015-2025.
19. (c) Denmark, S. E.; Almstead, N. G. Tetrahedron 1992, 48, 5565-5578.
20. (d) Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1993, 115, 3133-3139.
21. (e) Springer, J. B.; DeBoard, J.; Corcoran, R. C. Tetrahedron Lett. 1995 36, 8733-8736.
22. For reviews, see: (f) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 256-272. (g) Shambayati, S.; Schreiber, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming I Eds. Pereamon; New York, 1991: Vol. 1. p 283.
23. For reviews, see: (f) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 256-272. (g) Shambayati, S.; Schreiber, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming I Eds. Pereamon; New York, 1991: Vol. 1. p 283.
24. 2 complexes as potential intermediates, see refs 5g and 1c and references therein.
25. Engler, T. A.; Scheibe, C.; Iyengar, R. J. Org. Ghent. 1997, 62, 8274-8275.
26. Cavitt, S. B.; Sarrafizadeh, R. H.; Gardner, P. D. J. Org. Chem. 1962, 27, 1211-1216.
27. This preparation followed the procedure of Ishii, H.; Ohtake, R.; Ohida, H.; Mitsui, H.; Ikeda, N. J. Pharm. Soc. Jpn. 1970, 90, 1283-1289.