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Dimers of Cyclobutene-1,2-dicarbonitrile and 1,3-Butadiene-2,3- dicarbonitrile: Preparation and Chemistry
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12-Energiehyperfläche Thermolyse van syn und anti-Tricyclo[4.2.0.02, 5]octan. Experimentelle und Theoretische Untersuchungen. Chem. Ber. 1980, 113, 1153. (f) Dave, P. R.; Duddu, R.; Li, J.; Surapaneni, R.; Gilardi, R. Tetrahedron Lett. 1998, 39, 5481. (g) Bakkern, F. J. A. D.; Schröer, F.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron Lett. 1998, 39, 9531-9534.
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Conformation restrictions limit Stereomutation and fragmentation pathways of these systems relative to the thermolyses of free cyclobutane. For lead references into fragmentations of cyclobutanes, see: (a) Schaumann, E.; Ketcham, R. Angew. Chem., Int. Ed. Engl. 1982, 21, 225. (b) Lewis, D. K.; Glenar, D. A.; Kalra, B. L.; Baldwin, J. W.; Cianciosi, S. J. J. Am. Chem. Soc. 1987, 709, 7225-7227. (c) Chickos, J. S.; Annamalai, A.; Keiderling, T. A. J. Am. Chem. Soc. 1986, 108, 4398-4402. (d) Doubleday, C., Jr. J. Am. Chem. Soc. 1993, 115, 11968-11983. (e) Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 2001, 123, 4069-4072. For studies of related systems, see: (f) Khuong, K. S.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 14867-14883.
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Conformation restrictions limit Stereomutation and fragmentation pathways of these systems relative to the thermolyses of free cyclobutane. For lead references into fragmentations of cyclobutanes, see: (a) Schaumann, E.; Ketcham, R. Angew. Chem., Int. Ed. Engl. 1982, 21, 225. (b) Lewis, D. K.; Glenar, D. A.; Kalra, B. L.; Baldwin, J. W.; Cianciosi, S. J. J. Am. Chem. Soc. 1987, 709, 7225-7227. (c) Chickos, J. S.; Annamalai, A.; Keiderling, T. A. J. Am. Chem. Soc. 1986, 108, 4398-4402. (d) Doubleday, C., Jr. J. Am. Chem. Soc. 1993, 115, 11968-11983. (e) Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 2001, 123, 4069-4072. For studies of related systems, see: (f) Khuong, K. S.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 14867-14883.
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Conformation restrictions limit Stereomutation and fragmentation pathways of these systems relative to the thermolyses of free cyclobutane. For lead references into fragmentations of cyclobutanes, see: (a) Schaumann, E.; Ketcham, R. Angew. Chem., Int. Ed. Engl. 1982, 21, 225. (b) Lewis, D. K.; Glenar, D. A.; Kalra, B. L.; Baldwin, J. W.; Cianciosi, S. J. J. Am. Chem. Soc. 1987, 709, 7225-7227. (c) Chickos, J. S.; Annamalai, A.; Keiderling, T. A. J. Am. Chem. Soc. 1986, 108, 4398-4402. (d) Doubleday, C., Jr. J. Am. Chem. Soc. 1993, 115, 11968-11983. (e) Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 2001, 123, 4069-4072. For studies of related systems, see: (f) Khuong, K. S.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 14867-14883.
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Conformation restrictions limit Stereomutation and fragmentation pathways of these systems relative to the thermolyses of free cyclobutane. For lead references into fragmentations of cyclobutanes, see: (a) Schaumann, E.; Ketcham, R. Angew. Chem., Int. Ed. Engl. 1982, 21, 225. (b) Lewis, D. K.; Glenar, D. A.; Kalra, B. L.; Baldwin, J. W.; Cianciosi, S. J. J. Am. Chem. Soc. 1987, 709, 7225-7227. (c) Chickos, J. S.; Annamalai, A.; Keiderling, T. A. J. Am. Chem. Soc. 1986, 108, 4398-4402. (d) Doubleday, C., Jr. J. Am. Chem. Soc. 1993, 115, 11968-11983. (e) Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 2001, 123, 4069-4072. For studies of related systems, see: (f) Khuong, K. S.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 14867-14883.
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Conformation restrictions limit Stereomutation and fragmentation pathways of these systems relative to the thermolyses of free cyclobutane. For lead references into fragmentations of cyclobutanes, see: (a) Schaumann, E.; Ketcham, R. Angew. Chem., Int. Ed. Engl. 1982, 21, 225. (b) Lewis, D. K.; Glenar, D. A.; Kalra, B. L.; Baldwin, J. W.; Cianciosi, S. J. J. Am. Chem. Soc. 1987, 709, 7225-7227. (c) Chickos, J. S.; Annamalai, A.; Keiderling, T. A. J. Am. Chem. Soc. 1986, 108, 4398-4402. (d) Doubleday, C., Jr. J. Am. Chem. Soc. 1993, 115, 11968-11983. (e) Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 2001, 123, 4069-4072. For studies of related systems, see: (f) Khuong, K. S.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 14867-14883.
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Conformation restrictions limit Stereomutation and fragmentation pathways of these systems relative to the thermolyses of free cyclobutane. For lead references into fragmentations of cyclobutanes, see: (a) Schaumann, E.; Ketcham, R. Angew. Chem., Int. Ed. Engl. 1982, 21, 225. (b) Lewis, D. K.; Glenar, D. A.; Kalra, B. L.; Baldwin, J. W.; Cianciosi, S. J. J. Am. Chem. Soc. 1987, 709, 7225-7227. (c) Chickos, J. S.; Annamalai, A.; Keiderling, T. A. J. Am. Chem. Soc. 1986, 108, 4398-4402. (d) Doubleday, C., Jr. J. Am. Chem. Soc. 1993, 115, 11968-11983. (e) Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 2001, 123, 4069-4072. For studies of related systems, see: (f) Khuong, K. S.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 14867-14883.
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For examples of related cycloaddition/fragmentations, see: (c) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (d) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (e) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (f) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (g) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (h) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (i) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 325-331. (j) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (k) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (l) Mehta, G.; Reddy, A. V.; Srikrishna, A. J. Chem. Soc., Perkin Trans. 1 1986, 291-297. (m) White, J. D.; Kim, J.; Drapela N. E. J. Am. Chem. Soc. 2000, 122, 8665.
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For examples of related cycloaddition/fragmentations, see: (c) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (d) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (e) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (f) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (g) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (h) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (i) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 325-331. (j) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (k) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (l) Mehta, G.; Reddy, A. V.; Srikrishna, A. J. Chem. Soc., Perkin Trans. 1 1986, 291-297. (m) White, J. D.; Kim, J.; Drapela N. E. J. Am. Chem. Soc. 2000, 122, 8665.
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For examples of related cycloaddition/fragmentations, see: (c) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (d) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (e) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (f) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (g) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (h) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (i) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 325-331. (j) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (k) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (l) Mehta, G.; Reddy, A. V.; Srikrishna, A. J. Chem. Soc., Perkin Trans. 1 1986, 291-297. (m) White, J. D.; Kim, J.; Drapela N. E. J. Am. Chem. Soc. 2000, 122, 8665.
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For examples of related cycloaddition/fragmentations, see: (c) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (d) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (e) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (f) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (g) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (h) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (i) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 325-331. (j) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (k) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (l) Mehta, G.; Reddy, A. V.; Srikrishna, A. J. Chem. Soc., Perkin Trans. 1 1986, 291-297. (m) White, J. D.; Kim, J.; Drapela N. E. J. Am. Chem. Soc. 2000, 122, 8665.
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For examples of related cycloaddition/fragmentations, see: (c) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (d) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (e) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (f) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (g) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (h) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (i) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 325-331. (j) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (k) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (l) Mehta, G.; Reddy, A. V.; Srikrishna, A. J. Chem. Soc., Perkin Trans. 1 1986, 291-297. (m) White, J. D.; Kim, J.; Drapela N. E. J. Am. Chem. Soc. 2000, 122, 8665.
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For examples of related cycloaddition/fragmentations, see: (c) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (d) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (e) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (f) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (g) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (h) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (i) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 325-331. (j) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (k) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (l) Mehta, G.; Reddy, A. V.; Srikrishna, A. J. Chem. Soc., Perkin Trans. 1 1986, 291-297. (m) White, J. D.; Kim, J.; Drapela N. E. J. Am. Chem. Soc. 2000, 122, 8665.
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For examples of related cycloaddition/fragmentations, see: (c) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (d) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (e) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (f) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (g) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (h) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (i) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 325-331. (j) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (k) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (l) Mehta, G.; Reddy, A. V.; Srikrishna, A. J. Chem. Soc., Perkin Trans. 1 1986, 291-297. (m) White, J. D.; Kim, J.; Drapela N. E. J. Am. Chem. Soc. 2000, 122, 8665.
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For examples of related cycloaddition/fragmentations, see: (c) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (d) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (e) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (f) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (g) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (h) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (i) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 325-331. (j) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (k) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (l) Mehta, G.; Reddy, A. V.; Srikrishna, A. J. Chem. Soc., Perkin Trans. 1 1986, 291-297. (m) White, J. D.; Kim, J.; Drapela N. E. J. Am. Chem. Soc. 2000, 122, 8665.
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For examples of related cycloaddition/fragmentations, see: (c) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (d) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (e) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (f) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (g) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (h) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (i) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 325-331. (j) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (k) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (l) Mehta, G.; Reddy, A. V.; Srikrishna, A. J. Chem. Soc., Perkin Trans. 1 1986, 291-297. (m) White, J. D.; Kim, J.; Drapela N. E. J. Am. Chem. Soc. 2000, 122, 8665.
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Prinzbach, H.1
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28
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37049089965
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-
For examples of related cycloaddition/fragmentations, see: (c) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (d) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (e) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (f) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (g) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (h) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (i) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 325-331. (j) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (k) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (l) Mehta, G.; Reddy, A. V.; Srikrishna, A. J. Chem. Soc., Perkin Trans. 1 1986, 291-297. (m) White, J. D.; Kim, J.; Drapela N. E. J. Am. Chem. Soc. 2000, 122, 8665.
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Mehta, G.1
Reddy, A.V.2
Srikrishna, A.3
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29
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0034644425
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-
For examples of related cycloaddition/fragmentations, see: (c) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (d) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (e) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (f) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (g) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (h) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (i) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 325-331. (j) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (k) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (l) Mehta, G.; Reddy, A. V.; Srikrishna, A. J. Chem. Soc., Perkin Trans. 1 1986, 291-297. (m) White, J. D.; Kim, J.; Drapela N. E. J. Am. Chem. Soc. 2000, 122, 8665.
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White, J.D.1
Kim, J.2
Drapela, N.E.3
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(a) Deak, H. L.; Stokes, S. S.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 5152-5153.
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Deak, H.L.1
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31
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0037065297
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For the preparation of related cycloadducts, see: (b) Limanto, J.; Tallarico, J. A.; Porter, J. R.; Khuong, S. K.; Houk, K. N.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 14748-14758. (c) Tallarico, J. A.; Randall, M. L.; Snapper, M. L. J. Am. Chem. Soc. 1996, 118, 9196-9197.
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Limanto, J.1
Tallarico, J.A.2
Porter, J.R.3
Khuong, S.K.4
Houk, K.N.5
Snapper, M.L.6
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32
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0029825282
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For the preparation of related cycloadducts, see: (b) Limanto, J.; Tallarico, J. A.; Porter, J. R.; Khuong, S. K.; Houk, K. N.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 14748-14758. (c) Tallarico, J. A.; Randall, M. L.; Snapper, M. L. J. Am. Chem. Soc. 1996, 118, 9196-9197.
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Tallarico, J.A.1
Randall, M.L.2
Snapper, M.L.3
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33
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0001185733
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Viehe, H. G.; Merenyi, R.; Stella, L.; Janousek, Z. Angew. Chem., Int. Ed. Engl. 1979, 18, 917-932.
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Viehe, H.G.1
Merenyi, R.2
Stella, L.3
Janousek, Z.4
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34
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33845550778
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(a) Takahashi, M.; Uchino, T.; Ohno, K.; Tamura, Y.; Ikeda, M. J. Org. Chem. 1983, 48, 4241-4247.
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Takahashi, M.1
Uchino, T.2
Ohno, K.3
Tamura, Y.4
Ikeda, M.5
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35
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0001644337
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(b) Pirrung, M.; Chang, V. K.; DeAmicis, C. V. J. Am. Chem. Soc. 1989, 111, 5824-5831.
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Pirrung, M.1
Chang, V.K.2
DeAmicis, C.V.3
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36
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0029084414
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Williams, I. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U. H.; Grabowski, E. J. Tetrahedron Lett. 1995, 36, 5461-5464.
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Williams, I.M.1
Jobson, R.B.2
Yasuda, N.3
Marchesini, G.4
Dolling, U.H.5
Grabowski, E.J.6
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37
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13644270051
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-
note
-
2O at room temperature under Ar atmosphere for 1 days.
-
-
-
-
38
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0000478319
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-
For a review, see: Shapiro, R. H. Org. React. 1976, 23, 405-423.
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(1976)
Org. React.
, vol.23
, pp. 405-423
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Shapiro, R.H.1
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39
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13644264455
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Purchased from Aldrich Chemical Co.
-
Purchased from Aldrich Chemical Co.
-
-
-
-
40
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13644252714
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note
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With 50% yield based on 50% conversion.
-
-
-
-
41
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0019948481
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Smith, A. B., III.; Branca, S. J.; Pilla, N. N.; Guaciaro, M. A. J. Org. Chem. 1982, 47, 1855-1869.
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(1982)
J. Org. Chem.
, vol.47
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Smith III, A.B.1
Branca, S.J.2
Pilla, N.N.3
Guaciaro, M.A.4
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42
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13644250398
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note
-
1H NMR on the crude reaction mixture.
-
-
-
-
43
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13644258762
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-
note
-
While the fragmentations are likely to proceed through biradical intermediates, the terms symmetry-allowed and symmetry-forbidden are used to describe the stereochemical changes occurring between the fused cyclobutane starting materials and the corresponding cyclooctadiene products.
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