Electron transfer photochemistry of geraniol and (E,E)-farnesol. A novel 'tandem', 1,5-cyclization, intramolecular capture

Journal of the American Chemical Society

Volumn 118, Issue 45, 1996, Pages 10947-10953

  Weng, Hengxin ^a   Scarlata, Christopher ^a   Roth, Heinz D ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 OXABICYCLO[3.3.0]OCTANE DERIVATIVE; BICYCLO[3.3.0]OCTANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029982118     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962206z     Document Type: Article

References (89)

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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. cis-trans isomerizations. of cyclopropane systems: (j) Wong, P. C.; Arnold, D. R. Tetrahedron Lett. 1979, 2101. (k) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210. (l) Gassman, P. G.; Mlinarie-Majerski, K. J. Org. Chem. 1986, 51, 2397.
21. 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. cis-trans isomerizations. of cyclopropane systems: (j) Wong, P. C.; Arnold, D. R. Tetrahedron Lett. 1979, 2101. (k) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210. (l) Gassman, P. G.; Mlinarie-Majerski, K. J. Org. Chem. 1986, 51, 2397.
22. 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. cis-trans isomerizations. of cyclopropane systems: (j) Wong, P. C.; Arnold, D. R. Tetrahedron Lett. 1979, 2101. (k) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210. (l) Gassman, P. G.; Mlinarie-Majerski, K. J. Org. Chem. 1986, 51, 2397.
23. 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. cis-trans isomerizations. of cyclopropane systems: (j) Wong, P. C.; Arnold, D. R. Tetrahedron Lett. 1979, 2101. (k) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210. (l) Gassman, P. G.; Mlinarie-Majerski, K. J. Org. Chem. 1986, 51, 2397.
24. 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. cis-trans isomerizations. of cyclopropane systems: (j) Wong, P. C.; Arnold, D. R. Tetrahedron Lett. 1979, 2101. (k) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210. (l) Gassman, P. G.; Mlinarie-Majerski, K. J. Org. Chem. 1986, 51, 2397.
25. 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. cis-trans isomerizations. of cyclopropane systems: (j) Wong, P. C.; Arnold, D. R. Tetrahedron Lett. 1979, 2101. (k) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210. (l) Gassman, P. G.; Mlinarie-Majerski, K. J. Org. Chem. 1986, 51, 2397.
26. 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. cis-trans isomerizations. of cyclopropane systems: (j) Wong, P. C.; Arnold, D. R. Tetrahedron Lett. 1979, 2101. (k) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210. (l) Gassman, P. G.; Mlinarie-Majerski, K. J. Org. Chem. 1986, 51, 2397.
27. 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. cis-trans isomerizations. of cyclopropane systems: (j) Wong, P. C.; Arnold, D. R. Tetrahedron Lett. 1979, 2101. (k) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210. (l) Gassman, P. G.; Mlinarie-Majerski, K. J. Org. Chem. 1986, 51, 2397.
28. 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. cis-trans isomerizations. of cyclopropane systems: (j) Wong, P. C.; Arnold, D. R. Tetrahedron Lett. 1979, 2101. (k) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210. (l) Gassman, P. G.; Mlinarie-Majerski, K. J. Org. Chem. 1986, 51, 2397.
29. 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. cis-trans isomerizations. of cyclopropane systems: (j) Wong, P. C.; Arnold, D. R. Tetrahedron Lett. 1979, 2101. (k) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210. (l) Gassman, P. G.; Mlinarie-Majerski, K. J. Org. Chem. 1986, 51, 2397.
30. 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. cis-trans isomerizations. of cyclopropane systems: (j) Wong, P. C.; Arnold, D. R. Tetrahedron Lett. 1979, 2101. (k) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210. (l) Gassman, P. G.; Mlinarie-Majerski, K. J. Org. Chem. 1986, 51, 2397.
31. 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. cis-trans isomerizations. of cyclopropane systems: (j) Wong, P. C.; Arnold, D. R. Tetrahedron Lett. 1979, 2101. (k) Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1981, 103, 7210. (l) Gassman, P. G.; Mlinarie-Majerski, K. J. Org. Chem. 1986, 51, 2397.
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49. (a) For analogous reactions in sodium dodecyl sulfate micelles see: Hoffmann, U.; Gao, Y.; Pandey, B.; Klinge, S.; Warzecha, K.-D.; Krüger, C.; Roth, H. D.; Demuth, M. J. Am. Chem. Soc., 1993, 115, 10358-10359. (b) For analogous reactions in acetonitrile-water see: Warzecha, K.-D.; Xing, X.; Demuth, M.; Goddard, R.; Kessler, M.; Krüger, C. Helv. Chim. Acta, 1995, 78, 2065-2076
50. (a) For analogous reactions in sodium dodecyl sulfate micelles see: Hoffmann, U.; Gao, Y.; Pandey, B.; Klinge, S.; Warzecha, K.-D.; Krüger, C.; Roth, H. D.; Demuth, M. J. Am. Chem. Soc., 1993, 115, 10358-10359. (b) For analogous reactions in acetonitrile-water see: Warzecha, K.-D.; Xing, X.; Demuth, M.; Goddard, R.; Kessler, M.; Krüger, C. Helv. Chim. Acta, 1995, 78, 2065-2076
51. NMR spectral data for compounds 3-7 are available as Supporting Information. In the bicyclic compounds, 4-7, the first stereochemical indicator designates the ring fusion; for 4 and 5, the second indicator signifies the stereochemical relation at C6 relative to C1; for 6 and 7, the second and third indicators signify the stereochemical relation at C2 and C6, respectively, relative to C1.
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