Studies on Mercury(II)-Mediated Opening of Bi- and Tercyclopropane Arrays

Journal of Organic Chemistry

Volumn 62, Issue 14, 1997, Pages 4653-4664

  Barrett, Anthony G M ^a   Tam, William ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000985430     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970464o     Document Type: Article

References (47)

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8. For a second total synthesis of FR-900848, see: (a) Falck, J. R.; Mekonnen, B.; Yu, J.; Lai, J. Y. J. Am. Chem. Soc. 1996, 118, 6096. For a second total synthesis of U-106305, see: (b) Charette, A. B.; Helene, L. J. Am. Chem. Soc. 1996, 118, 10327.
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14. For reviews on cleavage of cyclopropanes, see: (a) Preston, P. M.; Tennant, G. Chem. Rev. 1972, 72, 627. (b) DePuy, C. H. Top. Curr. Chem. 1973, 40, 73. (c) Gibson, D. H.; DePuy, C. H. Chem. Rev. 1974, 74, 605. (d) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (e) Rappoport, Z., Ed. The Chemistry of the Cyclopropyl Group, Parts 1 and 2; J. Wiley and Sons: London, 1987.
15. For reviews on cleavage of cyclopropanes, see: (a) Preston, P. M.; Tennant, G. Chem. Rev. 1972, 72, 627. (b) DePuy, C. H. Top. Curr. Chem. 1973, 40, 73. (c) Gibson, D. H.; DePuy, C. H. Chem. Rev. 1974, 74, 605. (d) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (e) Rappoport, Z., Ed. The Chemistry of the Cyclopropyl Group, Parts 1 and 2; J. Wiley and Sons: London, 1987.
16. For reviews on cleavage of cyclopropanes, see: (a) Preston, P. M.; Tennant, G. Chem. Rev. 1972, 72, 627. (b) DePuy, C. H. Top. Curr. Chem. 1973, 40, 73. (c) Gibson, D. H.; DePuy, C. H. Chem. Rev. 1974, 74, 605. (d) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (e) Rappoport, Z., Ed. The Chemistry of the Cyclopropyl Group, Parts 1 and 2; J. Wiley and Sons: London, 1987.
17. For reviews on cleavage of cyclopropanes, see: (a) Preston, P. M.; Tennant, G. Chem. Rev. 1972, 72, 627. (b) DePuy, C. H. Top. Curr. Chem. 1973, 40, 73. (c) Gibson, D. H.; DePuy, C. H. Chem. Rev. 1974, 74, 605. (d) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (e) Rappoport, Z., Ed. The Chemistry of the Cyclopropyl Group, Parts 1 and 2; J. Wiley and Sons: London, 1987.
18. For reviews on cleavage of cyclopropanes, see: (a) Preston, P. M.; Tennant, G. Chem. Rev. 1972, 72, 627. (b) DePuy, C. H. Top. Curr. Chem. 1973, 40, 73. (c) Gibson, D. H.; DePuy, C. H. Chem. Rev. 1974, 74, 605. (d) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (e) Rappoport, Z., Ed. The Chemistry of the Cyclopropyl Group, Parts 1 and 2; J. Wiley and Sons: London, 1987.
19. For examples in mercury-induced ring opening of cyclopropanes, see: (a) Lukina, R.; Gladshetein, M. Dokl. Akad. Nauk SSSR 1950, 71, 65. (b) DePuy, C. H.; MsGuirk, R. H. J. Am. Chem. Soc. 1973, 95, 2366. (c) Collum, D. B.; Mohamadi, F.; Hallock, J. S. J. Am. Chem. Soc. 1983, 105, 6882. (d) Collum, D. B.; Still, W. C.; Mohamadi, F. J. Am. Chem. Soc. 1986, 108, 2094. (e) Lambert, J. B.; Chelius, E. C.; Bible, R. H., Jr.; Hajdu, E. J. Am. Chem. Soc. 1991, 113, 1331. (f) Kocovsky, P.; Srogl, J.; Pour, M.; Gogoll, A. J. Am. Chem. Soc. 1994, 116, 186. (g) Kocovsky, P.; Grech, J. M.; Mitchell, W. J. Org. Chem. 1995, 60, 1482.
20. For examples in mercury-induced ring opening of cyclopropanes, see: (a) Lukina, R.; Gladshetein, M. Dokl. Akad. Nauk SSSR 1950, 71, 65. (b) DePuy, C. H.; MsGuirk, R. H. J. Am. Chem. Soc. 1973, 95, 2366. (c) Collum, D. B.; Mohamadi, F.; Hallock, J. S. J. Am. Chem. Soc. 1983, 105, 6882. (d) Collum, D. B.; Still, W. C.; Mohamadi, F. J. Am. Chem. Soc. 1986, 108, 2094. (e) Lambert, J. B.; Chelius, E. C.; Bible, R. H., Jr.; Hajdu, E. J. Am. Chem. Soc. 1991, 113, 1331. (f) Kocovsky, P.; Srogl, J.; Pour, M.; Gogoll, A. J. Am. Chem. Soc. 1994, 116, 186. (g) Kocovsky, P.; Grech, J. M.; Mitchell, W. J. Org. Chem. 1995, 60, 1482.
21. For examples in mercury-induced ring opening of cyclopropanes, see: (a) Lukina, R.; Gladshetein, M. Dokl. Akad. Nauk SSSR 1950, 71, 65. (b) DePuy, C. H.; MsGuirk, R. H. J. Am. Chem. Soc. 1973, 95, 2366. (c) Collum, D. B.; Mohamadi, F.; Hallock, J. S. J. Am. Chem. Soc. 1983, 105, 6882. (d) Collum, D. B.; Still, W. C.; Mohamadi, F. J. Am. Chem. Soc. 1986, 108, 2094. (e) Lambert, J. B.; Chelius, E. C.; Bible, R. H., Jr.; Hajdu, E. J. Am. Chem. Soc. 1991, 113, 1331. (f) Kocovsky, P.; Srogl, J.; Pour, M.; Gogoll, A. J. Am. Chem. Soc. 1994, 116, 186. (g) Kocovsky, P.; Grech, J. M.; Mitchell, W. J. Org. Chem. 1995, 60, 1482.
22. For examples in mercury-induced ring opening of cyclopropanes, see: (a) Lukina, R.; Gladshetein, M. Dokl. Akad. Nauk SSSR 1950, 71, 65. (b) DePuy, C. H.; MsGuirk, R. H. J. Am. Chem. Soc. 1973, 95, 2366. (c) Collum, D. B.; Mohamadi, F.; Hallock, J. S. J. Am. Chem. Soc. 1983, 105, 6882. (d) Collum, D. B.; Still, W. C.; Mohamadi, F. J. Am. Chem. Soc. 1986, 108, 2094. (e) Lambert, J. B.; Chelius, E. C.; Bible, R. H., Jr.; Hajdu, E. J. Am. Chem. Soc. 1991, 113, 1331. (f) Kocovsky, P.; Srogl, J.; Pour, M.; Gogoll, A. J. Am. Chem. Soc. 1994, 116, 186. (g) Kocovsky, P.; Grech, J. M.; Mitchell, W. J. Org. Chem. 1995, 60, 1482.
23. For examples in mercury-induced ring opening of cyclopropanes, see: (a) Lukina, R.; Gladshetein, M. Dokl. Akad. Nauk SSSR 1950, 71, 65. (b) DePuy, C. H.; MsGuirk, R. H. J. Am. Chem. Soc. 1973, 95, 2366. (c) Collum, D. B.; Mohamadi, F.; Hallock, J. S. J. Am. Chem. Soc. 1983, 105, 6882. (d) Collum, D. B.; Still, W. C.; Mohamadi, F. J. Am. Chem. Soc. 1986, 108, 2094. (e) Lambert, J. B.; Chelius, E. C.; Bible, R. H., Jr.; Hajdu, E. J. Am. Chem. Soc. 1991, 113, 1331. (f) Kocovsky, P.; Srogl, J.; Pour, M.; Gogoll, A. J. Am. Chem. Soc. 1994, 116, 186. (g) Kocovsky, P.; Grech, J. M.; Mitchell, W. J. Org. Chem. 1995, 60, 1482.
24. For examples in mercury-induced ring opening of cyclopropanes, see: (a) Lukina, R.; Gladshetein, M. Dokl. Akad. Nauk SSSR 1950, 71, 65. (b) DePuy, C. H.; MsGuirk, R. H. J. Am. Chem. Soc. 1973, 95, 2366. (c) Collum, D. B.; Mohamadi, F.; Hallock, J. S. J. Am. Chem. Soc. 1983, 105, 6882. (d) Collum, D. B.; Still, W. C.; Mohamadi, F. J. Am. Chem. Soc. 1986, 108, 2094. (e) Lambert, J. B.; Chelius, E. C.; Bible, R. H., Jr.; Hajdu, E. J. Am. Chem. Soc. 1991, 113, 1331. (f) Kocovsky, P.; Srogl, J.; Pour, M.; Gogoll, A. J. Am. Chem. Soc. 1994, 116, 186. (g) Kocovsky, P.; Grech, J. M.; Mitchell, W. J. Org. Chem. 1995, 60, 1482.
25. For examples in mercury-induced ring opening of cyclopropanes, see: (a) Lukina, R.; Gladshetein, M. Dokl. Akad. Nauk SSSR 1950, 71, 65. (b) DePuy, C. H.; MsGuirk, R. H. J. Am. Chem. Soc. 1973, 95, 2366. (c) Collum, D. B.; Mohamadi, F.; Hallock, J. S. J. Am. Chem. Soc. 1983, 105, 6882. (d) Collum, D. B.; Still, W. C.; Mohamadi, F. J. Am. Chem. Soc. 1986, 108, 2094. (e) Lambert, J. B.; Chelius, E. C.; Bible, R. H., Jr.; Hajdu, E. J. Am. Chem. Soc. 1991, 113, 1331. (f) Kocovsky, P.; Srogl, J.; Pour, M.; Gogoll, A. J. Am. Chem. Soc. 1994, 116, 186. (g) Kocovsky, P.; Grech, J. M.; Mitchell, W. J. Org. Chem. 1995, 60, 1482.
26. For representative examples of opening of cyclopropanes by metals other than mercury, see the follow. Thallium: (a) Kocovsky, P.; Pour, M.; Gogoll, A. Hanus, V.; Smrcina, M. J. Am. Chem. Soc. 1990, 112, 6735. (b) Kocovsky, P.; Srogl, J.; Pour, M.; Gogoll, A. J. Am. Chem. Soc. 1994, 116, 186. Palladium: (c) Bäckvall, J. E.; Björkman, E. E.; Pettersson, L.; Siegbahn, P.; Strich, A. J. Am. Chem. Soc. 1985, 107, 7408. (d) Blomberg, M. R. A.; Siegbahn, P. E. M.; Bäckvall, J. E. J. Am. Chem. Soc. 1987, 109, 4405. Platinum: (e) Ikura, K.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc, 1992, 114, 1520. (f) Stewart, F. F.; Neilsen, W. D.; Ekeland, R. E.; Larsen, R. D.; Jennings, P. W. Organometallics 1993, 12, 4858. Rhodium: (g) Gassman, P. G.; Bunser, S. M. Tetrahedron Lett. 1983, 24, 3431. Iridium:
27. For representative examples of opening of cyclopropanes by metals other than mercury, see the follow. Thallium: (a) Kocovsky, P.; Pour, M.; Gogoll, A. Hanus, V.; Smrcina, M. J. Am. Chem. Soc. 1990, 112, 6735. (b) Kocovsky, P.; Srogl, J.; Pour, M.; Gogoll, A. J. Am. Chem. Soc. 1994, 116, 186. Palladium: (c) Bäckvall, J. E.; Björkman, E. E.; Pettersson, L.; Siegbahn, P.; Strich, A. J. Am. Chem. Soc. 1985, 107, 7408. (d) Blomberg, M. R. A.; Siegbahn, P. E. M.; Bäckvall, J. E. J. Am. Chem. Soc. 1987, 109, 4405. Platinum: (e) Ikura, K.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc, 1992, 114, 1520. (f) Stewart, F. F.; Neilsen, W. D.; Ekeland, R. E.; Larsen, R. D.; Jennings, P. W. Organometallics 1993, 12, 4858. Rhodium: (g) Gassman, P. G.; Bunser, S. M. Tetrahedron Lett. 1983, 24, 3431. Iridium:
28. For representative examples of opening of cyclopropanes by metals other than mercury, see the follow. Thallium: (a) Kocovsky, P.; Pour, M.; Gogoll, A. Hanus, V.; Smrcina, M. J. Am. Chem. Soc. 1990, 112, 6735. (b) Kocovsky, P.; Srogl, J.; Pour, M.; Gogoll, A. J. Am. Chem. Soc. 1994, 116, 186. Palladium: (c) Bäckvall, J. E.; Björkman, E. E.; Pettersson, L.; Siegbahn, P.; Strich, A. J. Am. Chem. Soc. 1985, 107, 7408. (d) Blomberg, M. R. A.; Siegbahn, P. E. M.; Bäckvall, J. E. J. Am. Chem. Soc. 1987, 109, 4405. Platinum: (e) Ikura, K.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc, 1992, 114, 1520. (f) Stewart, F. F.; Neilsen, W. D.; Ekeland, R. E.; Larsen, R. D.; Jennings, P. W. Organometallics 1993, 12, 4858. Rhodium: (g) Gassman, P. G.; Bunser, S. M. Tetrahedron Lett. 1983, 24, 3431. Iridium:
29. For representative examples of opening of cyclopropanes by metals other than mercury, see the follow. Thallium: (a) Kocovsky, P.; Pour, M.; Gogoll, A. Hanus, V.; Smrcina, M. J. Am. Chem. Soc. 1990, 112, 6735. (b) Kocovsky, P.; Srogl, J.; Pour, M.; Gogoll, A. J. Am. Chem. Soc. 1994, 116, 186. Palladium: (c) Bäckvall, J. E.; Björkman, E. E.; Pettersson, L.; Siegbahn, P.; Strich, A. J. Am. Chem. Soc. 1985, 107, 7408. (d) Blomberg, M. R. A.; Siegbahn, P. E. M.; Bäckvall, J. E. J. Am. Chem. Soc. 1987, 109, 4405. Platinum: (e) Ikura, K.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc, 1992, 114, 1520. (f) Stewart, F. F.; Neilsen, W. D.; Ekeland, R. E.; Larsen, R. D.; Jennings, P. W. Organometallics 1993, 12, 4858. Rhodium: (g) Gassman, P. G.; Bunser, S. M. Tetrahedron Lett. 1983, 24, 3431. Iridium:
30. For representative examples of opening of cyclopropanes by metals other than mercury, see the follow. Thallium: (a) Kocovsky, P.; Pour, M.; Gogoll, A. Hanus, V.; Smrcina, M. J. Am. Chem. Soc. 1990, 112, 6735. (b) Kocovsky, P.; Srogl, J.; Pour, M.; Gogoll, A. J. Am. Chem. Soc. 1994, 116, 186. Palladium: (c) Bäckvall, J. E.; Björkman, E. E.; Pettersson, L.; Siegbahn, P.; Strich, A. J. Am. Chem. Soc. 1985, 107, 7408. (d) Blomberg, M. R. A.; Siegbahn, P. E. M.; Bäckvall, J. E. J. Am. Chem. Soc. 1987, 109, 4405. Platinum: (e) Ikura, K.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc, 1992, 114, 1520. (f) Stewart, F. F.; Neilsen, W. D.; Ekeland, R. E.; Larsen, R. D.; Jennings, P. W. Organometallics 1993, 12, 4858. Rhodium: (g) Gassman, P. G.; Bunser, S. M. Tetrahedron Lett. 1983, 24, 3431. Iridium:
31. For representative examples of opening of cyclopropanes by metals other than mercury, see the follow. Thallium: (a) Kocovsky, P.; Pour, M.; Gogoll, A. Hanus, V.; Smrcina, M. J. Am. Chem. Soc. 1990, 112, 6735. (b) Kocovsky, P.; Srogl, J.; Pour, M.; Gogoll, A. J. Am. Chem. Soc. 1994, 116, 186. Palladium: (c) Bäckvall, J. E.; Björkman, E. E.; Pettersson, L.; Siegbahn, P.; Strich, A. J. Am. Chem. Soc. 1985, 107, 7408. (d) Blomberg, M. R. A.; Siegbahn, P. E. M.; Bäckvall, J. E. J. Am. Chem. Soc. 1987, 109, 4405. Platinum: (e) Ikura, K.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc, 1992, 114, 1520. (f) Stewart, F. F.; Neilsen, W. D.; Ekeland, R. E.; Larsen, R. D.; Jennings, P. W. Organometallics 1993, 12, 4858. Rhodium: (g) Gassman, P. G.; Bunser, S. M. Tetrahedron Lett. 1983, 24, 3431. Iridium:
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