CIDNP study and ab-initio calculations of rigid vinylcyclopropane systems: Evidence for delocalized 'ring-closed' radical cations

Tetrahedron

Volumn 53, Issue 29, 1997, Pages 10051-10070

  Roth, Heinz D ^a   Weng, Hengxin ^a   Herbertz, Torsten ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSINTHOL; BETA THUYONE; BICYCLO COMPOUND; BICYCLO[3.1.0]HEXANE DERIVATIVE; CYCLOPROPANE DERIVATIVE; SABINENE; TERPENE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; DRUG STRUCTURE; ELECTRON SPIN RESONANCE; MOLECULAR DYNAMICS; PRIORITY JOURNAL; STEREOCHEMISTRY; THEORY; THERMODYNAMICS;

EID: 0030876129     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00347-5     Document Type: Article

References (92)

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12. quadricyclane to norbornadiene radical cation: (a) Roth, H. D.; Schilling, M. L. M.; Jones, G., II J. Am. Chem. Soc. 1981, 103, 1246-1248. (b) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210-7217. methylenecyclopropane rearrangement: (c) Takahashi, Y.; Mukai, T.; Miyashi T. J. Am. Chem. Soc. 1983, 105, 6511-6513. (d) Miyashi, T.; Takahashi, Y.; Mukai, T.; Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1985, 107, 1079-1080. bicyclobutane to cyclobutene rearrangement: (e) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1985, 107, 4075. (f) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1986, 108, 4227. (g) Arnold, A.; Burger, U.; Gerson, F.; Kloster-Jensen, E.; Schmidlin, S. P. J. Am. Chem. Soc. 1993, 115, 4271-4281. vinylcyclopropane rearrangement: (h) Dinnocenzo, J. P.; Schmittel, M. J. Am. Chem. Soc. 1987, 109, 1561-1562. (i) Dinnocenzo, J.P.; Conlon, D. A. J. Am. Chem. Soc. 1988, 110, 2324-2326.
13. quadricyclane to norbornadiene radical cation: (a) Roth, H. D.; Schilling, M. L. M.; Jones, G., II J. Am. Chem. Soc. 1981, 103, 1246-1248. (b) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210-7217. methylenecyclopropane rearrangement: (c) Takahashi, Y.; Mukai, T.; Miyashi T. J. Am. Chem. Soc. 1983, 105, 6511-6513. (d) Miyashi, T.; Takahashi, Y.; Mukai, T.; Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1985, 107, 1079-1080. bicyclobutane to cyclobutene rearrangement: (e) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1985, 107, 4075. (f) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1986, 108, 4227. (g) Arnold, A.; Burger, U.; Gerson, F.; Kloster-Jensen, E.; Schmidlin, S. P. J. Am. Chem. Soc. 1993, 115, 4271-4281. vinylcyclopropane rearrangement: (h) Dinnocenzo, J. P.; Schmittel, M. J. Am. Chem. Soc. 1987, 109, 1561-1562. (i) Dinnocenzo, J.P.; Conlon, D. A. J. Am. Chem. Soc. 1988, 110, 2324-2326.
14. quadricyclane to norbornadiene radical cation: (a) Roth, H. D.; Schilling, M. L. M.; Jones, G., II J. Am. Chem. Soc. 1981, 103, 1246-1248. (b) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210-7217. methylenecyclopropane rearrangement: (c) Takahashi, Y.; Mukai, T.; Miyashi T. J. Am. Chem. Soc. 1983, 105, 6511-6513. (d) Miyashi, T.; Takahashi, Y.; Mukai, T.; Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1985, 107, 1079-1080. bicyclobutane to cyclobutene rearrangement: (e) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1985, 107, 4075. (f) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1986, 108, 4227. (g) Arnold, A.; Burger, U.; Gerson, F.; Kloster-Jensen, E.; Schmidlin, S. P. J. Am. Chem. Soc. 1993, 115, 4271-4281. vinylcyclopropane rearrangement: (h) Dinnocenzo, J. P.; Schmittel, M. J. Am. Chem. Soc. 1987, 109, 1561-1562. (i) Dinnocenzo, J.P.; Conlon, D. A. J. Am. Chem. Soc. 1988, 110, 2324-2326.
15. quadricyclane to norbornadiene radical cation: (a) Roth, H. D.; Schilling, M. L. M.; Jones, G., II J. Am. Chem. Soc. 1981, 103, 1246-1248. (b) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210-7217. methylenecyclopropane rearrangement: (c) Takahashi, Y.; Mukai, T.; Miyashi T. J. Am. Chem. Soc. 1983, 105, 6511-6513. (d) Miyashi, T.; Takahashi, Y.; Mukai, T.; Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1985, 107, 1079-1080. bicyclobutane to cyclobutene rearrangement: (e) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1985, 107, 4075. (f) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1986, 108, 4227. (g) Arnold, A.; Burger, U.; Gerson, F.; Kloster-Jensen, E.; Schmidlin, S. P. J. Am. Chem. Soc. 1993, 115, 4271-4281. vinylcyclopropane rearrangement: (h) Dinnocenzo, J. P.; Schmittel, M. J. Am. Chem. Soc. 1987, 109, 1561-1562. (i) Dinnocenzo, J.P.; Conlon, D. A. J. Am. Chem. Soc. 1988, 110, 2324-2326.
16. quadricyclane to norbornadiene radical cation: (a) Roth, H. D.; Schilling, M. L. M.; Jones, G., II J. Am. Chem. Soc. 1981, 103, 1246-1248. (b) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210-7217. methylenecyclopropane rearrangement: (c) Takahashi, Y.; Mukai, T.; Miyashi T. J. Am. Chem. Soc. 1983, 105, 6511-6513. (d) Miyashi, T.; Takahashi, Y.; Mukai, T.; Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1985, 107, 1079-1080. bicyclobutane to cyclobutene rearrangement: (e) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1985, 107, 4075. (f) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1986, 108, 4227. (g) Arnold, A.; Burger, U.; Gerson, F.; Kloster-Jensen, E.; Schmidlin, S. P. J. Am. Chem. Soc. 1993, 115, 4271-4281. vinylcyclopropane rearrangement: (h) Dinnocenzo, J. P.; Schmittel, M. J. Am. Chem. Soc. 1987, 109, 1561-1562. (i) Dinnocenzo, J.P.; Conlon, D. A. J. Am. Chem. Soc. 1988, 110, 2324-2326.
17. quadricyclane to norbornadiene radical cation: (a) Roth, H. D.; Schilling, M. L. M.; Jones, G., II J. Am. Chem. Soc. 1981, 103, 1246-1248. (b) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210-7217. methylenecyclopropane rearrangement: (c) Takahashi, Y.; Mukai, T.; Miyashi T. J. Am. Chem. Soc. 1983, 105, 6511-6513. (d) Miyashi, T.; Takahashi, Y.; Mukai, T.; Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1985, 107, 1079-1080. bicyclobutane to cyclobutene rearrangement: (e) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1985, 107, 4075. (f) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1986, 108, 4227. (g) Arnold, A.; Burger, U.; Gerson, F.; Kloster-Jensen, E.; Schmidlin, S. P. J. Am. Chem. Soc. 1993, 115, 4271-4281. vinylcyclopropane rearrangement: (h) Dinnocenzo, J. P.; Schmittel, M. J. Am. Chem. Soc. 1987, 109, 1561-1562. (i) Dinnocenzo, J.P.; Conlon, D. A. J. Am. Chem. Soc. 1988, 110, 2324-2326.
18. quadricyclane to norbornadiene radical cation: (a) Roth, H. D.; Schilling, M. L. M.; Jones, G., II J. Am. Chem. Soc. 1981, 103, 1246-1248. (b) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210-7217. methylenecyclopropane rearrangement: (c) Takahashi, Y.; Mukai, T.; Miyashi T. J. Am. Chem. Soc. 1983, 105, 6511-6513. (d) Miyashi, T.; Takahashi, Y.; Mukai, T.; Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1985, 107, 1079-1080. bicyclobutane to cyclobutene rearrangement: (e) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1985, 107, 4075. (f) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1986, 108, 4227. (g) Arnold, A.; Burger, U.; Gerson, F.; Kloster-Jensen, E.; Schmidlin, S. P. J. Am. Chem. Soc. 1993, 115, 4271-4281. vinylcyclopropane rearrangement: (h) Dinnocenzo, J. P.; Schmittel, M. J. Am. Chem. Soc. 1987, 109, 1561-1562. (i) Dinnocenzo, J.P.; Conlon, D. A. J. Am. Chem. Soc. 1988, 110, 2324-2326.
19. quadricyclane to norbornadiene radical cation: (a) Roth, H. D.; Schilling, M. L. M.; Jones, G., II J. Am. Chem. Soc. 1981, 103, 1246-1248. (b) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210-7217. methylenecyclopropane rearrangement: (c) Takahashi, Y.; Mukai, T.; Miyashi T. J. Am. Chem. Soc. 1983, 105, 6511-6513. (d) Miyashi, T.; Takahashi, Y.; Mukai, T.; Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1985, 107, 1079-1080. bicyclobutane to cyclobutene rearrangement: (e) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1985, 107, 4075. (f) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1986, 108, 4227. (g) Arnold, A.; Burger, U.; Gerson, F.; Kloster-Jensen, E.; Schmidlin, S. P. J. Am. Chem. Soc. 1993, 115, 4271-4281. vinylcyclopropane rearrangement: (h) Dinnocenzo, J. P.; Schmittel, M. J. Am. Chem. Soc. 1987, 109, 1561-1562. (i) Dinnocenzo, J.P.; Conlon, D. A. J. Am. Chem. Soc. 1988, 110, 2324-2326.
20. quadricyclane to norbornadiene radical cation: (a) Roth, H. D.; Schilling, M. L. M.; Jones, G., II J. Am. Chem. Soc. 1981, 103, 1246-1248. (b) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210-7217. methylenecyclopropane rearrangement: (c) Takahashi, Y.; Mukai, T.; Miyashi T. J. Am. Chem. Soc. 1983, 105, 6511-6513. (d) Miyashi, T.; Takahashi, Y.; Mukai, T.; Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1985, 107, 1079-1080. bicyclobutane to cyclobutene rearrangement: (e) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1985, 107, 4075. (f) Gassman, P. G.; Hay, B. A. J. Am. Chem. Soc. 1986, 108, 4227. (g) Arnold, A.; Burger, U.; Gerson, F.; Kloster-Jensen, E.; Schmidlin, S. P. J. Am. Chem. Soc. 1993, 115, 4271-4281. vinylcyclopropane rearrangement: (h) Dinnocenzo, J. P.; Schmittel, M. J. Am. Chem. Soc. 1987, 109, 1561-1562. (i) Dinnocenzo, J.P.; Conlon, D. A. J. Am. Chem. Soc. 1988, 110, 2324-2326.
21. cyclopropane systems: (a) Rao, V. R.; Hixson, S. S. J. Am. Chem. Soc. 1979, 101, 6458. (b) Hixson, S. S.; Xing, Y. Tetrahedron Lett. 1991, 32, 173-174. (c) Dinnocenzo, J. P.; Todd, W. P.; Simpson, T. R.; Gould, I. R. J. Am. Chem. Soc. 1990, 112, 2462-2464. (d) Dinnocenzo, J. P.; Lieberman, D. R.; Simpson, T. R. J. Am. Chem. Soc. 1993, 115, 366-367. bicyclobutane systems: (e) Gassman, P. G.; Olson, K. D.; Walter, L.; Yamaguchi, R. J. Am. Chem. Soc. 1981, 103, 4977. (f) Gassman, P. G.; Olson, K. D. J. Am. Chem. Soc. 1982, 104, 3740. vinylcyclobutane systems: (g) Arnold, D. R.; Du, X. J. J. Am. Chem. Soc. 1989, 111, 7666. (h) Arnold, D. R.; Du, X. Can. J. Chem. 1994, 72, 403. (i) Zhou, D., Sheikh, M.; Roth, H. D. Tet. Lett. 1996, 37, 2385.
22. cyclopropane systems: (a) Rao, V. R.; Hixson, S. S. J. Am. Chem. Soc. 1979, 101, 6458. (b) Hixson, S. S.; Xing, Y. Tetrahedron Lett. 1991, 32, 173-174. (c) Dinnocenzo, J. P.; Todd, W. P.; Simpson, T. R.; Gould, I. R. J. Am. Chem. Soc. 1990, 112, 2462-2464. (d) Dinnocenzo, J. P.; Lieberman, D. R.; Simpson, T. R. J. Am. Chem. Soc. 1993, 115, 366-367. bicyclobutane systems: (e) Gassman, P. G.; Olson, K. D.; Walter, L.; Yamaguchi, R. J. Am. Chem. Soc. 1981, 103, 4977. (f) Gassman, P. G.; Olson, K. D. J. Am. Chem. Soc. 1982, 104, 3740. vinylcyclobutane systems: (g) Arnold, D. R.; Du, X. J. J. Am. Chem. Soc. 1989, 111, 7666. (h) Arnold, D. R.; Du, X. Can. J. Chem. 1994, 72, 403. (i) Zhou, D., Sheikh, M.; Roth, H. D. Tet. Lett. 1996, 37, 2385.
23. cyclopropane systems: (a) Rao, V. R.; Hixson, S. S. J. Am. Chem. Soc. 1979, 101, 6458. (b) Hixson, S. S.; Xing, Y. Tetrahedron Lett. 1991, 32, 173-174. (c) Dinnocenzo, J. P.; Todd, W. P.; Simpson, T. R.; Gould, I. R. J. Am. Chem. Soc. 1990, 112, 2462-2464. (d) Dinnocenzo, J. P.; Lieberman, D. R.; Simpson, T. R. J. Am. Chem. Soc. 1993, 115, 366-367. bicyclobutane systems: (e) Gassman, P. G.; Olson, K. D.; Walter, L.; Yamaguchi, R. J. Am. Chem. Soc. 1981, 103, 4977. (f) Gassman, P. G.; Olson, K. D. J. Am. Chem. Soc. 1982, 104, 3740. vinylcyclobutane systems: (g) Arnold, D. R.; Du, X. J. J. Am. Chem. Soc. 1989, 111, 7666. (h) Arnold, D. R.; Du, X. Can. J. Chem. 1994, 72, 403. (i) Zhou, D., Sheikh, M.; Roth, H. D. Tet. Lett. 1996, 37, 2385.
24. cyclopropane systems: (a) Rao, V. R.; Hixson, S. S. J. Am. Chem. Soc. 1979, 101, 6458. (b) Hixson, S. S.; Xing, Y. Tetrahedron Lett. 1991, 32, 173-174. (c) Dinnocenzo, J. P.; Todd, W. P.; Simpson, T. R.; Gould, I. R. J. Am. Chem. Soc. 1990, 112, 2462-2464. (d) Dinnocenzo, J. P.; Lieberman, D. R.; Simpson, T. R. J. Am. Chem. Soc. 1993, 115, 366-367. bicyclobutane systems: (e) Gassman, P. G.; Olson, K. D.; Walter, L.; Yamaguchi, R. J. Am. Chem. Soc. 1981, 103, 4977. (f) Gassman, P. G.; Olson, K. D. J. Am. Chem. Soc. 1982, 104, 3740. vinylcyclobutane systems: (g) Arnold, D. R.; Du, X. J. J. Am. Chem. Soc. 1989, 111, 7666. (h) Arnold, D. R.; Du, X. Can. J. Chem. 1994, 72, 403. (i) Zhou, D., Sheikh, M.; Roth, H. D. Tet. Lett. 1996, 37, 2385.
25. cyclopropane systems: (a) Rao, V. R.; Hixson, S. S. J. Am. Chem. Soc. 1979, 101, 6458. (b) Hixson, S. S.; Xing, Y. Tetrahedron Lett. 1991, 32, 173-174. (c) Dinnocenzo, J. P.; Todd, W. P.; Simpson, T. R.; Gould, I. R. J. Am. Chem. Soc. 1990, 112, 2462-2464. (d) Dinnocenzo, J. P.; Lieberman, D. R.; Simpson, T. R. J. Am. Chem. Soc. 1993, 115, 366-367. bicyclobutane systems: (e) Gassman, P. G.; Olson, K. D.; Walter, L.; Yamaguchi, R. J. Am. Chem. Soc. 1981, 103, 4977. (f) Gassman, P. G.; Olson, K. D. J. Am. Chem. Soc. 1982, 104, 3740. vinylcyclobutane systems: (g) Arnold, D. R.; Du, X. J. J. Am. Chem. Soc. 1989, 111, 7666. (h) Arnold, D. R.; Du, X. Can. J. Chem. 1994, 72, 403. (i) Zhou, D., Sheikh, M.; Roth, H. D. Tet. Lett. 1996, 37, 2385.
26. cyclopropane systems: (a) Rao, V. R.; Hixson, S. S. J. Am. Chem. Soc. 1979, 101, 6458. (b) Hixson, S. S.; Xing, Y. Tetrahedron Lett. 1991, 32, 173-174. (c) Dinnocenzo, J. P.; Todd, W. P.; Simpson, T. R.; Gould, I. R. J. Am. Chem. Soc. 1990, 112, 2462-2464. (d) Dinnocenzo, J. P.; Lieberman, D. R.; Simpson, T. R. J. Am. Chem. Soc. 1993, 115, 366-367. bicyclobutane systems: (e) Gassman, P. G.; Olson, K. D.; Walter, L.; Yamaguchi, R. J. Am. Chem. Soc. 1981, 103, 4977. (f) Gassman, P. G.; Olson, K. D. J. Am. Chem. Soc. 1982, 104, 3740. vinylcyclobutane systems: (g) Arnold, D. R.; Du, X. J. J. Am. Chem. Soc. 1989, 111, 7666. (h) Arnold, D. R.; Du, X. Can. J. Chem. 1994, 72, 403. (i) Zhou, D., Sheikh, M.; Roth, H. D. Tet. Lett. 1996, 37, 2385.
27. cyclopropane systems: (a) Rao, V. R.; Hixson, S. S. J. Am. Chem. Soc. 1979, 101, 6458. (b) Hixson, S. S.; Xing, Y. Tetrahedron Lett. 1991, 32, 173-174. (c) Dinnocenzo, J. P.; Todd, W. P.; Simpson, T. R.; Gould, I. R. J. Am. Chem. Soc. 1990, 112, 2462-2464. (d) Dinnocenzo, J. P.; Lieberman, D. R.; Simpson, T. R. J. Am. Chem. Soc. 1993, 115, 366-367. bicyclobutane systems: (e) Gassman, P. G.; Olson, K. D.; Walter, L.; Yamaguchi, R. J. Am. Chem. Soc. 1981, 103, 4977. (f) Gassman, P. G.; Olson, K. D. J. Am. Chem. Soc. 1982, 104, 3740. vinylcyclobutane systems: (g) Arnold, D. R.; Du, X. J. J. Am. Chem. Soc. 1989, 111, 7666. (h) Arnold, D. R.; Du, X. Can. J. Chem. 1994, 72, 403. (i) Zhou, D., Sheikh, M.; Roth, H. D. Tet. Lett. 1996, 37, 2385.
28. cyclopropane systems: (a) Rao, V. R.; Hixson, S. S. J. Am. Chem. Soc. 1979, 101, 6458. (b) Hixson, S. S.; Xing, Y. Tetrahedron Lett. 1991, 32, 173-174. (c) Dinnocenzo, J. P.; Todd, W. P.; Simpson, T. R.; Gould, I. R. J. Am. Chem. Soc. 1990, 112, 2462-2464. (d) Dinnocenzo, J. P.; Lieberman, D. R.; Simpson, T. R. J. Am. Chem. Soc. 1993, 115, 366-367. bicyclobutane systems: (e) Gassman, P. G.; Olson, K. D.; Walter, L.; Yamaguchi, R. J. Am. Chem. Soc. 1981, 103, 4977. (f) Gassman, P. G.; Olson, K. D. J. Am. Chem. Soc. 1982, 104, 3740. vinylcyclobutane systems: (g) Arnold, D. R.; Du, X. J. J. Am. Chem. Soc. 1989, 111, 7666. (h) Arnold, D. R.; Du, X. Can. J. Chem. 1994, 72, 403. (i) Zhou, D., Sheikh, M.; Roth, H. D. Tet. Lett. 1996, 37, 2385.
29. cyclopropane systems: (a) Rao, V. R.; Hixson, S. S. J. Am. Chem. Soc. 1979, 101, 6458. (b) Hixson, S. S.; Xing, Y. Tetrahedron Lett. 1991, 32, 173-174. (c) Dinnocenzo, J. P.; Todd, W. P.; Simpson, T. R.; Gould, I. R. J. Am. Chem. Soc. 1990, 112, 2462-2464. (d) Dinnocenzo, J. P.; Lieberman, D. R.; Simpson, T. R. J. Am. Chem. Soc. 1993, 115, 366-367. bicyclobutane systems: (e) Gassman, P. G.; Olson, K. D.; Walter, L.; Yamaguchi, R. J. Am. Chem. Soc. 1981, 103, 4977. (f) Gassman, P. G.; Olson, K. D. J. Am. Chem. Soc. 1982, 104, 3740. vinylcyclobutane systems: (g) Arnold, D. R.; Du, X. J. J. Am. Chem. Soc. 1989, 111, 7666. (h) Arnold, D. R.; Du, X. Can. J. Chem. 1994, 72, 403. (i) Zhou, D., Sheikh, M.; Roth, H. D. Tet. Lett. 1996, 37, 2385.
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