Steroids as photonic wires. Z → E olefin photoisomerization involving ketone singlet → triplet switches by through-bond energy transfer

Journal of the American Chemical Society

Volumn 119, Issue 34, 1997, Pages 7945-7953

  Agyin, Joseph K ^a   Timberlake, Larry D ^a   Morrison, Harry ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

STEROID;

ARTICLE; CHROMATOGRAPHY; ENERGY TRANSFER; ISOMERISM; LIGHT ABSORPTION; PHOTOCHEMISTRY; PHOTOLYSIS; SYNTHESIS;

EID: 0030758957     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963261a     Document Type: Article

References (69)

1. Organic Photochemistry. Part 113. Part 112: Jiang, S. A.; Xiao, C.; Morrison, H. J. Org. Chem. 1996, 61, 7045-7055.
2. (a) Preliminary communication: Agyin, J. K.; Morrison, H.; Siemiarczuk, A. J. Am. Chem. Soc. 1995, 117, 3875-3876. (b) Abstracted from the Doctoral Dissertation of J. K. Agyin, Purdue University, August, 1996.
3. (a) Preliminary communication: Agyin, J. K.; Morrison, H.; Siemiarczuk, A. J. Am. Chem. Soc. 1995, 117, 3875-3876. (b) Abstracted from the Doctoral Dissertation of J. K. Agyin, Purdue University, August, 1996.
4. For an overview, see: Tolles, W. M. In Nanotechnology. Molecularly Designed Materials; Chow, G.-M., Gonsalves, K. E., Eds.; ACS Symp. Ser. No. 622; American Chemical Society: Washington, DC, 1996; Chapter 1, pp 1-19. See also: Balzani, V.; Scandola, F. Supramolecular Photochemistry; Ellis Horwood: Chichester, Great Britain, 1991.
5. For an overview, see: Tolles, W. M. In Nanotechnology. Molecularly Designed Materials; Chow, G.-M., Gonsalves, K. E., Eds.; ACS Symp. Ser. No. 622; American Chemical Society: Washington, DC, 1996; Chapter 1, pp 1-19. See also: Balzani, V.; Scandola, F. Supramolecular Photochemistry; Ellis Horwood: Chichester, Great Britain, 1991.
6. For an overview, see: Tolles, W. M. In Nanotechnology. Molecularly Designed Materials; Chow, G.-M., Gonsalves, K. E., Eds.; ACS Symp. Ser. No. 622; American Chemical Society: Washington, DC, 1996; Chapter 1, pp 1-19. See also: Balzani, V.; Scandola, F. Supramolecular Photochemistry; Ellis Horwood: Chichester, Great Britain, 1991.
7. Examples with leading references: Wagner, R. A.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocian, D. F. J. Am. Chem. Soc. 1996, 118, 3996-3997. Zhou, Q.; Swager, T. M. J. Am. Chem. Soc. 1995, 117, 12593-12602.
8. Examples with leading references: Wagner, R. A.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocian, D. F. J. Am. Chem. Soc. 1996, 118, 3996-3997. Zhou, Q.; Swager, T. M. J. Am. Chem. Soc. 1995, 117, 12593-12602.
9. Representative examples: (a) Kroon, J.; Oliver, A. M.; Paddon-Row, M. N.; Verhoeven, J. W. J. Am. Chem. Soc. 1990, 112, 4868-4873. (b) Shephard, M. J.; Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1994, 116, 5328-5333. (c) Ren, Y.; Wang, Z.; Zhu, H.; Weininger, S. J.; McGimpsey, W. G. J. Am. Chem. Soc. 1995, 117, 4367-4373. (d) Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933-3951. (e) Kszynski, P.; Friedl, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601-620. (f) Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1993, 115, 2952-2960. (g) Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, I.; Noshimura, Y. J. Org. Chem. 1995, 60, 7177-7185. (h) Holl, N.; Port, H.; Wolf, H. C.; Strobel, H.; Effenberger, F. Chem. Phys. 1993, 176, 215-220. (i) Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227-6228. (j) Würthner, F.; Vollmer, M. S.; Effenberger, F.; Emele, P.; Meyer, D. U.; Port, H.; Wolf, H. C. J. Am. Chem. Soc. 1995, 117, 8090-8099. (k) Schanze, K. S.; Sauer, K. J. Am. Chem. Soc. 1988, 110, 1180-1186. (l) Vassilian, A.; Wishart, J. F.; van Hemelryck, B.; Schwarz, H.; Isied, S. S. J. Am. Chem. Soc. 1990, 112, 7278-7286. (m) Voyer, N.; LaMothe, J. Tetrahedron 1995, 51, 9241-9284. (n) Benniston, A. C.; Harriman, A.; Lynch, V. M. J. Am. Chem. Soc. 1995, 117, 5275-5291. (o) Watkins, D. M.; Fox, M. A. J. Am. Chem. Soc. 1994, 116, 6441-6442.
10. Representative examples: (a) Kroon, J.; Oliver, A. M.; Paddon-Row, M. N.; Verhoeven, J. W. J. Am. Chem. Soc. 1990, 112, 4868-4873. (b) Shephard, M. J.; Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1994, 116, 5328-5333. (c) Ren, Y.; Wang, Z.; Zhu, H.; Weininger, S. J.; McGimpsey, W. G. J. Am. Chem. Soc. 1995, 117, 4367-4373. (d) Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933-3951. (e) Kszynski, P.; Friedl, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601-620. (f) Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1993, 115, 2952-2960. (g) Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, I.; Noshimura, Y. J. Org. Chem. 1995, 60, 7177-7185. (h) Holl, N.; Port, H.; Wolf, H. C.; Strobel, H.; Effenberger, F. Chem. Phys. 1993, 176, 215-220. (i) Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227-6228. (j) Würthner, F.; Vollmer, M. S.; Effenberger, F.; Emele, P.; Meyer, D. U.; Port, H.; Wolf, H. C. J. Am. Chem. Soc. 1995, 117, 8090-8099. (k) Schanze, K. S.; Sauer, K. J. Am. Chem. Soc. 1988, 110, 1180-1186. (l) Vassilian, A.; Wishart, J. F.; van Hemelryck, B.; Schwarz, H.; Isied, S. S. J. Am. Chem. Soc. 1990, 112, 7278-7286. (m) Voyer, N.; LaMothe, J. Tetrahedron 1995, 51, 9241-9284. (n) Benniston, A. C.; Harriman, A.; Lynch, V. M. J. Am. Chem. Soc. 1995, 117, 5275-5291. (o) Watkins, D. M.; Fox, M. A. J. Am. Chem. Soc. 1994, 116, 6441-6442.
11. Representative examples: (a) Kroon, J.; Oliver, A. M.; Paddon-Row, M. N.; Verhoeven, J. W. J. Am. Chem. Soc. 1990, 112, 4868-4873. (b) Shephard, M. J.; Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1994, 116, 5328-5333. (c) Ren, Y.; Wang, Z.; Zhu, H.; Weininger, S. J.; McGimpsey, W. G. J. Am. Chem. Soc. 1995, 117, 4367-4373. (d) Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933-3951. (e) Kszynski, P.; Friedl, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601-620. (f) Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1993, 115, 2952-2960. (g) Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, I.; Noshimura, Y. J. Org. Chem. 1995, 60, 7177-7185. (h) Holl, N.; Port, H.; Wolf, H. C.; Strobel, H.; Effenberger, F. Chem. Phys. 1993, 176, 215-220. (i) Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227-6228. (j) Würthner, F.; Vollmer, M. S.; Effenberger, F.; Emele, P.; Meyer, D. U.; Port, H.; Wolf, H. C. J. Am. Chem. Soc. 1995, 117, 8090-8099. (k) Schanze, K. S.; Sauer, K. J. Am. Chem. Soc. 1988, 110, 1180-1186. (l) Vassilian, A.; Wishart, J. F.; van Hemelryck, B.; Schwarz, H.; Isied, S. S. J. Am. Chem. Soc. 1990, 112, 7278-7286. (m) Voyer, N.; LaMothe, J. Tetrahedron 1995, 51, 9241-9284. (n) Benniston, A. C.; Harriman, A.; Lynch, V. M. J. Am. Chem. Soc. 1995, 117, 5275-5291. (o) Watkins, D. M.; Fox, M. A. J. Am. Chem. Soc. 1994, 116, 6441-6442.
12. Representative examples: (a) Kroon, J.; Oliver, A. M.; Paddon-Row, M. N.; Verhoeven, J. W. J. Am. Chem. Soc. 1990, 112, 4868-4873. (b) Shephard, M. J.; Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1994, 116, 5328-5333. (c) Ren, Y.; Wang, Z.; Zhu, H.; Weininger, S. J.; McGimpsey, W. G. J. Am. Chem. Soc. 1995, 117, 4367-4373. (d) Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933-3951. (e) Kszynski, P.; Friedl, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601-620. (f) Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1993, 115, 2952-2960. (g) Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, I.; Noshimura, Y. J. Org. Chem. 1995, 60, 7177-7185. (h) Holl, N.; Port, H.; Wolf, H. C.; Strobel, H.; Effenberger, F. Chem. Phys. 1993, 176, 215-220. (i) Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227-6228. (j) Würthner, F.; Vollmer, M. S.; Effenberger, F.; Emele, P.; Meyer, D. U.; Port, H.; Wolf, H. C. J. Am. Chem. Soc. 1995, 117, 8090-8099. (k) Schanze, K. S.; Sauer, K. J. Am. Chem. Soc. 1988, 110, 1180-1186. (l) Vassilian, A.; Wishart, J. F.; van Hemelryck, B.; Schwarz, H.; Isied, S. S. J. Am. Chem. Soc. 1990, 112, 7278-7286. (m) Voyer, N.; LaMothe, J. Tetrahedron 1995, 51, 9241-9284. (n) Benniston, A. C.; Harriman, A.; Lynch, V. M. J. Am. Chem. Soc. 1995, 117, 5275-5291. (o) Watkins, D. M.; Fox, M. A. J. Am. Chem. Soc. 1994, 116, 6441-6442.
13. Representative examples: (a) Kroon, J.; Oliver, A. M.; Paddon-Row, M. N.; Verhoeven, J. W. J. Am. Chem. Soc. 1990, 112, 4868-4873. (b) Shephard, M. J.; Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1994, 116, 5328-5333. (c) Ren, Y.; Wang, Z.; Zhu, H.; Weininger, S. J.; McGimpsey, W. G. J. Am. Chem. Soc. 1995, 117, 4367-4373. (d) Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933-3951. (e) Kszynski, P.; Friedl, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601-620. (f) Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1993, 115, 2952-2960. (g) Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, I.; Noshimura, Y. J. Org. Chem. 1995, 60, 7177-7185. (h) Holl, N.; Port, H.; Wolf, H. C.; Strobel, H.; Effenberger, F. Chem. Phys. 1993, 176, 215-220. (i) Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227-6228. (j) Würthner, F.; Vollmer, M. S.; Effenberger, F.; Emele, P.; Meyer, D. U.; Port, H.; Wolf, H. C. J. Am. Chem. Soc. 1995, 117, 8090-8099. (k) Schanze, K. S.; Sauer, K. J. Am. Chem. Soc. 1988, 110, 1180-1186. (l) Vassilian, A.; Wishart, J. F.; van Hemelryck, B.; Schwarz, H.; Isied, S. S. J. Am. Chem. Soc. 1990, 112, 7278-7286. (m) Voyer, N.; LaMothe, J. Tetrahedron 1995, 51, 9241-9284. (n) Benniston, A. C.; Harriman, A.; Lynch, V. M. J. Am. Chem. Soc. 1995, 117, 5275-5291. (o) Watkins, D. M.; Fox, M. A. J. Am. Chem. Soc. 1994, 116, 6441-6442.
14. Representative examples: (a) Kroon, J.; Oliver, A. M.; Paddon-Row, M. N.; Verhoeven, J. W. J. Am. Chem. Soc. 1990, 112, 4868-4873. (b) Shephard, M. J.; Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1994, 116, 5328-5333. (c) Ren, Y.; Wang, Z.; Zhu, H.; Weininger, S. J.; McGimpsey, W. G. J. Am. Chem. Soc. 1995, 117, 4367-4373. (d) Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933-3951. (e) Kszynski, P.; Friedl, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601-620. (f) Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1993, 115, 2952-2960. (g) Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, I.; Noshimura, Y. J. Org. Chem. 1995, 60, 7177-7185. (h) Holl, N.; Port, H.; Wolf, H. C.; Strobel, H.; Effenberger, F. Chem. Phys. 1993, 176, 215-220. (i) Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227-6228. (j) Würthner, F.; Vollmer, M. S.; Effenberger, F.; Emele, P.; Meyer, D. U.; Port, H.; Wolf, H. C. J. Am. Chem. Soc. 1995, 117, 8090-8099. (k) Schanze, K. S.; Sauer, K. J. Am. Chem. Soc. 1988, 110, 1180-1186. (l) Vassilian, A.; Wishart, J. F.; van Hemelryck, B.; Schwarz, H.; Isied, S. S. J. Am. Chem. Soc. 1990, 112, 7278-7286. (m) Voyer, N.; LaMothe, J. Tetrahedron 1995, 51, 9241-9284. (n) Benniston, A. C.; Harriman, A.; Lynch, V. M. J. Am. Chem. Soc. 1995, 117, 5275-5291. (o) Watkins, D. M.; Fox, M. A. J. Am. Chem. Soc. 1994, 116, 6441-6442.
15. Representative examples: (a) Kroon, J.; Oliver, A. M.; Paddon-Row, M. N.; Verhoeven, J. W. J. Am. Chem. Soc. 1990, 112, 4868-4873. (b) Shephard, M. J.; Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1994, 116, 5328-5333. (c) Ren, Y.; Wang, Z.; Zhu, H.; Weininger, S. J.; McGimpsey, W. G. J. Am. Chem. Soc. 1995, 117, 4367-4373. (d) Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933-3951. (e) Kszynski, P.; Friedl, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601-620. (f) Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1993, 115, 2952-2960. (g) Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, I.; Noshimura, Y. J. Org. Chem. 1995, 60, 7177-7185. (h) Holl, N.; Port, H.; Wolf, H. C.; Strobel, H.; Effenberger, F. Chem. Phys. 1993, 176, 215-220. (i) Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227-6228. (j) Würthner, F.; Vollmer, M. S.; Effenberger, F.; Emele, P.; Meyer, D. U.; Port, H.; Wolf, H. C. J. Am. Chem. Soc. 1995, 117, 8090-8099. (k) Schanze, K. S.; Sauer, K. J. Am. Chem. Soc. 1988, 110, 1180-1186. (l) Vassilian, A.; Wishart, J. F.; van Hemelryck, B.; Schwarz, H.; Isied, S. S. J. Am. Chem. Soc. 1990, 112, 7278-7286. (m) Voyer, N.; LaMothe, J. Tetrahedron 1995, 51, 9241-9284. (n) Benniston, A. C.; Harriman, A.; Lynch, V. M. J. Am. Chem. Soc. 1995, 117, 5275-5291. (o) Watkins, D. M.; Fox, M. A. J. Am. Chem. Soc. 1994, 116, 6441-6442.
16. Representative examples: (a) Kroon, J.; Oliver, A. M.; Paddon-Row, M. N.; Verhoeven, J. W. J. Am. Chem. Soc. 1990, 112, 4868-4873. (b) Shephard, M. J.; Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1994, 116, 5328-5333. (c) Ren, Y.; Wang, Z.; Zhu, H.; Weininger, S. J.; McGimpsey, W. G. J. Am. Chem. Soc. 1995, 117, 4367-4373. (d) Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933-3951. (e) Kszynski, P.; Friedl, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601-620. (f) Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1993, 115, 2952-2960. (g) Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, I.; Noshimura, Y. J. Org. Chem. 1995, 60, 7177-7185. (h) Holl, N.; Port, H.; Wolf, H. C.; Strobel, H.; Effenberger, F. Chem. Phys. 1993, 176, 215-220. (i) Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227-6228. (j) Würthner, F.; Vollmer, M. S.; Effenberger, F.; Emele, P.; Meyer, D. U.; Port, H.; Wolf, H. C. J. Am. Chem. Soc. 1995, 117, 8090-8099. (k) Schanze, K. S.; Sauer, K. J. Am. Chem. Soc. 1988, 110, 1180-1186. (l) Vassilian, A.; Wishart, J. F.; van Hemelryck, B.; Schwarz, H.; Isied, S. S. J. Am. Chem. Soc. 1990, 112, 7278-7286. (m) Voyer, N.; LaMothe, J. Tetrahedron 1995, 51, 9241-9284. (n) Benniston, A. C.; Harriman, A.; Lynch, V. M. J. Am. Chem. Soc. 1995, 117, 5275-5291. (o) Watkins, D. M.; Fox, M. A. J. Am. Chem. Soc. 1994, 116, 6441-6442.
17. Representative examples: (a) Kroon, J.; Oliver, A. M.; Paddon-Row, M. N.; Verhoeven, J. W. J. Am. Chem. Soc. 1990, 112, 4868-4873. (b) Shephard, M. J.; Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1994, 116, 5328-5333. (c) Ren, Y.; Wang, Z.; Zhu, H.; Weininger, S. J.; McGimpsey, W. G. J. Am. Chem. Soc. 1995, 117, 4367-4373. (d) Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933-3951. (e) Kszynski, P.; Friedl, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601-620. (f) Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1993, 115, 2952-2960. (g) Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, I.; Noshimura, Y. J. Org. Chem. 1995, 60, 7177-7185. (h) Holl, N.; Port, H.; Wolf, H. C.; Strobel, H.; Effenberger, F. Chem. Phys. 1993, 176, 215-220. (i) Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227-6228. (j) Würthner, F.; Vollmer, M. S.; Effenberger, F.; Emele, P.; Meyer, D. U.; Port, H.; Wolf, H. C. J. Am. Chem. Soc. 1995, 117, 8090-8099. (k) Schanze, K. S.; Sauer, K. J. Am. Chem. Soc. 1988, 110, 1180-1186. (l) Vassilian, A.; Wishart, J. F.; van Hemelryck, B.; Schwarz, H.; Isied, S. S. J. Am. Chem. Soc. 1990, 112, 7278-7286. (m) Voyer, N.; LaMothe, J. Tetrahedron 1995, 51, 9241-9284. (n) Benniston, A. C.; Harriman, A.; Lynch, V. M. J. Am. Chem. Soc. 1995, 117, 5275-5291. (o) Watkins, D. M.; Fox, M. A. J. Am. Chem. Soc. 1994, 116, 6441-6442.
18. Representative examples: (a) Kroon, J.; Oliver, A. M.; Paddon-Row, M. N.; Verhoeven, J. W. J. Am. Chem. Soc. 1990, 112, 4868-4873. (b) Shephard, M. J.; Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1994, 116, 5328-5333. (c) Ren, Y.; Wang, Z.; Zhu, H.; Weininger, S. J.; McGimpsey, W. G. J. Am. Chem. Soc. 1995, 117, 4367-4373. (d) Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933-3951. (e) Kszynski, P.; Friedl, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601-620. (f) Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1993, 115, 2952-2960. (g) Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, I.; Noshimura, Y. J. Org. Chem. 1995, 60, 7177-7185. (h) Holl, N.; Port, H.; Wolf, H. C.; Strobel, H.; Effenberger, F. Chem. Phys. 1993, 176, 215-220. (i) Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227-6228. (j) Würthner, F.; Vollmer, M. S.; Effenberger, F.; Emele, P.; Meyer, D. U.; Port, H.; Wolf, H. C. J. Am. Chem. Soc. 1995, 117, 8090-8099. (k) Schanze, K. S.; Sauer, K. J. Am. Chem. Soc. 1988, 110, 1180-1186. (l) Vassilian, A.; Wishart, J. F.; van Hemelryck, B.; Schwarz, H.; Isied, S. S. J. Am. Chem. Soc. 1990, 112, 7278-7286. (m) Voyer, N.; LaMothe, J. Tetrahedron 1995, 51, 9241-9284. (n) Benniston, A. C.; Harriman, A.; Lynch, V. M. J. Am. Chem. Soc. 1995, 117, 5275-5291. (o) Watkins, D. M.; Fox, M. A. J. Am. Chem. Soc. 1994, 116, 6441-6442.
19. Representative examples: (a) Kroon, J.; Oliver, A. M.; Paddon-Row, M. N.; Verhoeven, J. W. J. Am. Chem. Soc. 1990, 112, 4868-4873. (b) Shephard, M. J.; Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1994, 116, 5328-5333. (c) Ren, Y.; Wang, Z.; Zhu, H.; Weininger, S. J.; McGimpsey, W. G. J. Am. Chem. Soc. 1995, 117, 4367-4373. (d) Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933-3951. (e) Kszynski, P.; Friedl, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601-620. (f) Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1993, 115, 2952-2960. (g) Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, I.; Noshimura, Y. J. Org. Chem. 1995, 60, 7177-7185. (h) Holl, N.; Port, H.; Wolf, H. C.; Strobel, H.; Effenberger, F. Chem. Phys. 1993, 176, 215-220. (i) Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227-6228. (j) Würthner, F.; Vollmer, M. S.; Effenberger, F.; Emele, P.; Meyer, D. U.; Port, H.; Wolf, H. C. J. Am. Chem. Soc. 1995, 117, 8090-8099. (k) Schanze, K. S.; Sauer, K. J. Am. Chem. Soc. 1988, 110, 1180-1186. (l) Vassilian, A.; Wishart, J. F.; van Hemelryck, B.; Schwarz, H.; Isied, S. S. J. Am. Chem. Soc. 1990, 112, 7278-7286. (m) Voyer, N.; LaMothe, J. Tetrahedron 1995, 51, 9241-9284. (n) Benniston, A. C.; Harriman, A.; Lynch, V. M. J. Am. Chem. Soc. 1995, 117, 5275-5291. (o) Watkins, D. M.; Fox, M. A. J. Am. Chem. Soc. 1994, 116, 6441-6442.
20. Representative examples: (a) Kroon, J.; Oliver, A. M.; Paddon-Row, M. N.; Verhoeven, J. W. J. Am. Chem. Soc. 1990, 112, 4868-4873. (b) Shephard, M. J.; Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1994, 116, 5328-5333. (c) Ren, Y.; Wang, Z.; Zhu, H.; Weininger, S. J.; McGimpsey, W. G. J. Am. Chem. Soc. 1995, 117, 4367-4373. (d) Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933-3951. (e) Kszynski, P.; Friedl, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601-620. (f) Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1993, 115, 2952-2960. (g) Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, I.; Noshimura, Y. J. Org. Chem. 1995, 60, 7177-7185. (h) Holl, N.; Port, H.; Wolf, H. C.; Strobel, H.; Effenberger, F. Chem. Phys. 1993, 176, 215-220. (i) Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227-6228. (j) Würthner, F.; Vollmer, M. S.; Effenberger, F.; Emele, P.; Meyer, D. U.; Port, H.; Wolf, H. C. J. Am. Chem. Soc. 1995, 117, 8090-8099. (k) Schanze, K. S.; Sauer, K. J. Am. Chem. Soc. 1988, 110, 1180-1186. (l) Vassilian, A.; Wishart, J. F.; van Hemelryck, B.; Schwarz, H.; Isied, S. S. J. Am. Chem. Soc. 1990, 112, 7278-7286. (m) Voyer, N.; LaMothe, J. Tetrahedron 1995, 51, 9241-9284. (n) Benniston, A. C.; Harriman, A.; Lynch, V. M. J. Am. Chem. Soc. 1995, 117, 5275-5291. (o) Watkins, D. M.; Fox, M. A. J. Am. Chem. Soc. 1994, 116, 6441-6442.
21. Representative examples: (a) Kroon, J.; Oliver, A. M.; Paddon-Row, M. N.; Verhoeven, J. W. J. Am. Chem. Soc. 1990, 112, 4868-4873. (b) Shephard, M. J.; Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1994, 116, 5328-5333. (c) Ren, Y.; Wang, Z.; Zhu, H.; Weininger, S. J.; McGimpsey, W. G. J. Am. Chem. Soc. 1995, 117, 4367-4373. (d) Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933-3951. (e) Kszynski, P.; Friedl, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601-620. (f) Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1993, 115, 2952-2960. (g) Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, I.; Noshimura, Y. J. Org. Chem. 1995, 60, 7177-7185. (h) Holl, N.; Port, H.; Wolf, H. C.; Strobel, H.; Effenberger, F. Chem. Phys. 1993, 176, 215-220. (i) Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227-6228. (j) Würthner, F.; Vollmer, M. S.; Effenberger, F.; Emele, P.; Meyer, D. U.; Port, H.; Wolf, H. C. J. Am. Chem. Soc. 1995, 117, 8090-8099. (k) Schanze, K. S.; Sauer, K. J. Am. Chem. Soc. 1988, 110, 1180-1186. (l) Vassilian, A.; Wishart, J. F.; van Hemelryck, B.; Schwarz, H.; Isied, S. S. J. Am. Chem. Soc. 1990, 112, 7278-7286. (m) Voyer, N.; LaMothe, J. Tetrahedron 1995, 51, 9241-9284. (n) Benniston, A. C.; Harriman, A.; Lynch, V. M. J. Am. Chem. Soc. 1995, 117, 5275-5291. (o) Watkins, D. M.; Fox, M. A. J. Am. Chem. Soc. 1994, 116, 6441-6442.
22. Representative examples: (a) Kroon, J.; Oliver, A. M.; Paddon-Row, M. N.; Verhoeven, J. W. J. Am. Chem. Soc. 1990, 112, 4868-4873. (b) Shephard, M. J.; Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1994, 116, 5328-5333. (c) Ren, Y.; Wang, Z.; Zhu, H.; Weininger, S. J.; McGimpsey, W. G. J. Am. Chem. Soc. 1995, 117, 4367-4373. (d) Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933-3951. (e) Kszynski, P.; Friedl, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601-620. (f) Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1993, 115, 2952-2960. (g) Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, I.; Noshimura, Y. J. Org. Chem. 1995, 60, 7177-7185. (h) Holl, N.; Port, H.; Wolf, H. C.; Strobel, H.; Effenberger, F. Chem. Phys. 1993, 176, 215-220. (i) Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227-6228. (j) Würthner, F.; Vollmer, M. S.; Effenberger, F.; Emele, P.; Meyer, D. U.; Port, H.; Wolf, H. C. J. Am. Chem. Soc. 1995, 117, 8090-8099. (k) Schanze, K. S.; Sauer, K. J. Am. Chem. Soc. 1988, 110, 1180-1186. (l) Vassilian, A.; Wishart, J. F.; van Hemelryck, B.; Schwarz, H.; Isied, S. S. J. Am. Chem. Soc. 1990, 112, 7278-7286. (m) Voyer, N.; LaMothe, J. Tetrahedron 1995, 51, 9241-9284. (n) Benniston, A. C.; Harriman, A.; Lynch, V. M. J. Am. Chem. Soc. 1995, 117, 5275-5291. (o) Watkins, D. M.; Fox, M. A. J. Am. Chem. Soc. 1994, 116, 6441-6442.
23. Representative examples: (a) Kroon, J.; Oliver, A. M.; Paddon-Row, M. N.; Verhoeven, J. W. J. Am. Chem. Soc. 1990, 112, 4868-4873. (b) Shephard, M. J.; Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1994, 116, 5328-5333. (c) Ren, Y.; Wang, Z.; Zhu, H.; Weininger, S. J.; McGimpsey, W. G. J. Am. Chem. Soc. 1995, 117, 4367-4373. (d) Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933-3951. (e) Kszynski, P.; Friedl, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601-620. (f) Paddon-Row, M. N.; Jordan, K. D. J. Am. Chem. Soc. 1993, 115, 2952-2960. (g) Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, I.; Noshimura, Y. J. Org. Chem. 1995, 60, 7177-7185. (h) Holl, N.; Port, H.; Wolf, H. C.; Strobel, H.; Effenberger, F. Chem. Phys. 1993, 176, 215-220. (i) Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227-6228. (j) Würthner, F.; Vollmer, M. S.; Effenberger, F.; Emele, P.; Meyer, D. U.; Port, H.; Wolf, H. C. J. Am. Chem. Soc. 1995, 117, 8090-8099. (k) Schanze, K. S.; Sauer, K. J. Am. Chem. Soc. 1988, 110, 1180-1186. (l) Vassilian, A.; Wishart, J. F.; van Hemelryck, B.; Schwarz, H.; Isied, S. S. J. Am. Chem. Soc. 1990, 112, 7278-7286. (m) Voyer, N.; LaMothe, J. Tetrahedron 1995, 51, 9241-9284. (n) Benniston, A. C.; Harriman, A.; Lynch, V. M. J. Am. Chem. Soc. 1995, 117, 5275-5291. (o) Watkins, D. M.; Fox, M. A. J. Am. Chem. Soc. 1994, 116, 6441-6442.
24. Recent reviews see: Paddon-Row, M. N.; Jordan, K. D. In Modern Models of Bonding Delocalization; Liebman, J. F., Greenberg, A., Eds.; VCH: New York, 1988; Vol. 6, ,Chapter 3. Jordan, K. D.; Paddon-Row, M. N. Chem. Rev. 1992, 92, 395-410. Verhoeven, J. W.; Kroon, J.; Paddon-Row, M. N.; Warman, J. M. In Supramolecular Chemistry; Balzani, V., De Cola, L., Eds.; Kluwer Academic Publishers: Dordrecht, 1992; pp 181-200.
25. Recent reviews see: Paddon-Row, M. N.; Jordan, K. D. In Modern Models of Bonding Delocalization; Liebman, J. F., Greenberg, A., Eds.; VCH: New York, 1988; Vol. 6, ,Chapter 3. Jordan, K. D.; Paddon-Row, M. N. Chem. Rev. 1992, 92, 395-410. Verhoeven, J. W.; Kroon, J.; Paddon-Row, M. N.; Warman, J. M. In Supramolecular Chemistry; Balzani, V., De Cola, L., Eds.; Kluwer Academic Publishers: Dordrecht, 1992; pp 181-200.
26. Recent reviews see: Paddon-Row, M. N.; Jordan, K. D. In Modern Models of Bonding Delocalization; Liebman, J. F., Greenberg, A., Eds.; VCH: New York, 1988; Vol. 6, ,Chapter 3. Jordan, K. D.; Paddon-Row, M. N. Chem. Rev. 1992, 92, 395-410. Verhoeven, J. W.; Kroon, J.; Paddon-Row, M. N.; Warman, J. M. In Supramolecular Chemistry; Balzani, V., De Cola, L., Eds.; Kluwer Academic Publishers: Dordrecht, 1992; pp 181-200.
27. (a) Wu, Z.-Z.; Morrison, H. J. Am. Chem. Soc. 1989, 111, 9267-9269.
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35. (d) Tong, Z.-H.; Yang, G.-Q.; Wu, S.-K. Acta Chim. Sin. (Engl. Ed.) 1989, 450. Tong, Z.-H.; Yang, G.-Q.; Wu, S.-K. Chinese J. Chem. 1990, 61. For related studies involving electron transfer, see: Closs, G. L. J. Phys. Chem. 1986, 90, 3673-3683. Closs, G. L.; Piotrowiak, P.; Miller, J. R. In Photochemical Energy Conversion; Norris, J. R., Jr., Meisel, D., Eds.; Elsevier; New York, 1989; p 23. Liang, N.; Miller, J. R.; Closs, G. L. J. Am. Chem. Soc. 1990, 112, 5353-5354. The seminal papers involving the study of energy transfer in steroids are the following: Latt, S. A.; Cheung, H. T.; Blout, E. R. J. Am. Chem. Soc. 1965, 87, 995-1003. Keller, R. A.; Dolby, L. J. J. Am. Chem. Soc. 1967, 89, 2768-2770. Keller, R. A.; Dolby, L. J. J. Am. Chem. Soc. 1969, 91, 1293-1299.
36. (d) Tong, Z.-H.; Yang, G.-Q.; Wu, S.-K. Acta Chim. Sin. (Engl. Ed.) 1989, 450. Tong, Z.-H.; Yang, G.-Q.; Wu, S.-K. Chinese J. Chem. 1990, 61. For related studies involving electron transfer, see: Closs, G. L. J. Phys. Chem. 1986, 90, 3673-3683. Closs, G. L.; Piotrowiak, P.; Miller, J. R. In Photochemical Energy Conversion; Norris, J. R., Jr., Meisel, D., Eds.; Elsevier; New York, 1989; p 23. Liang, N.; Miller, J. R.; Closs, G. L. J. Am. Chem. Soc. 1990, 112, 5353-5354. The seminal papers involving the study of energy transfer in steroids are the following: Latt, S. A.; Cheung, H. T.; Blout, E. R. J. Am. Chem. Soc. 1965, 87, 995-1003. Keller, R. A.; Dolby, L. J. J. Am. Chem. Soc. 1967, 89, 2768-2770. Keller, R. A.; Dolby, L. J. J. Am. Chem. Soc. 1969, 91, 1293-1299.
37. (d) Tong, Z.-H.; Yang, G.-Q.; Wu, S.-K. Acta Chim. Sin. (Engl. Ed.) 1989, 450. Tong, Z.-H.; Yang, G.-Q.; Wu, S.-K. Chinese J. Chem. 1990, 61. For related studies involving electron transfer, see: Closs, G. L. J. Phys. Chem. 1986, 90, 3673-3683. Closs, G. L.; Piotrowiak, P.; Miller, J. R. In Photochemical Energy Conversion; Norris, J. R., Jr., Meisel, D., Eds.; Elsevier; New York, 1989; p 23. Liang, N.; Miller, J. R.; Closs, G. L. J. Am. Chem. Soc. 1990, 112, 5353-5354. The seminal papers involving the study of energy transfer in steroids are the following: Latt, S. A.; Cheung, H. T.; Blout, E. R. J. Am. Chem. Soc. 1965, 87, 995-1003. Keller, R. A.; Dolby, L. J. J. Am. Chem. Soc. 1967, 89, 2768-2770. Keller, R. A.; Dolby, L. J. J. Am. Chem. Soc. 1969, 91, 1293-1299.
38. (d) Tong, Z.-H.; Yang, G.-Q.; Wu, S.-K. Acta Chim. Sin. (Engl. Ed.) 1989, 450. Tong, Z.-H.; Yang, G.-Q.; Wu, S.-K. Chinese J. Chem. 1990, 61. For related studies involving electron transfer, see: Closs, G. L. J. Phys. Chem. 1986, 90, 3673-3683. Closs, G. L.; Piotrowiak, P.; Miller, J. R. In Photochemical Energy Conversion; Norris, J. R., Jr., Meisel, D., Eds.; Elsevier; New York, 1989; p 23. Liang, N.; Miller, J. R.; Closs, G. L. J. Am. Chem. Soc. 1990, 112, 5353-5354. The seminal papers involving the study of energy transfer in steroids are the following: Latt, S. A.; Cheung, H. T.; Blout, E. R. J. Am. Chem. Soc. 1965, 87, 995-1003. Keller, R. A.; Dolby, L. J. J. Am. Chem. Soc. 1967, 89, 2768-2770. Keller, R. A.; Dolby, L. J. J. Am. Chem. Soc. 1969, 91, 1293-1299.
39. (d) Tong, Z.-H.; Yang, G.-Q.; Wu, S.-K. Acta Chim. Sin. (Engl. Ed.) 1989, 450. Tong, Z.-H.; Yang, G.-Q.; Wu, S.-K. Chinese J. Chem. 1990, 61. For related studies involving electron transfer, see: Closs, G. L. J. Phys. Chem. 1986, 90, 3673-3683. Closs, G. L.; Piotrowiak, P.; Miller, J. R. In Photochemical Energy Conversion; Norris, J. R., Jr., Meisel, D., Eds.; Elsevier; New York, 1989; p 23. Liang, N.; Miller, J. R.; Closs, G. L. J. Am. Chem. Soc. 1990, 112, 5353-5354. The seminal papers involving the study of energy transfer in steroids are the following: Latt, S. A.; Cheung, H. T.; Blout, E. R. J. Am. Chem. Soc. 1965, 87, 995-1003. Keller, R. A.; Dolby, L. J. J. Am. Chem. Soc. 1967, 89, 2768-2770. Keller, R. A.; Dolby, L. J. J. Am. Chem. Soc. 1969, 91, 1293-1299.
40. (d) Tong, Z.-H.; Yang, G.-Q.; Wu, S.-K. Acta Chim. Sin. (Engl. Ed.) 1989, 450. Tong, Z.-H.; Yang, G.-Q.; Wu, S.-K. Chinese J. Chem. 1990, 61. For related studies involving electron transfer, see: Closs, G. L. J. Phys. Chem. 1986, 90, 3673-3683. Closs, G. L.; Piotrowiak, P.; Miller, J. R. In Photochemical Energy Conversion; Norris, J. R., Jr., Meisel, D., Eds.; Elsevier; New York, 1989; p 23. Liang, N.; Miller, J. R.; Closs, G. L. J. Am. Chem. Soc. 1990, 112, 5353-5354. The seminal papers involving the study of energy transfer in steroids are the following: Latt, S. A.; Cheung, H. T.; Blout, E. R. J. Am. Chem. Soc. 1965, 87, 995-1003. Keller, R. A.; Dolby, L. J. J. Am. Chem. Soc. 1967, 89, 2768-2770. Keller, R. A.; Dolby, L. J. J. Am. Chem. Soc. 1969, 91, 1293-1299.
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54. 7d
55. 1
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59. A referee has noted that the comparable rate constants may be fortuitous given the difference in triplet energies represented by the naphthalene/benzophenone and ketone/olefin donor/acceptor pairs. Unfortunately, we had insufficient material to do a similar analysis of 4, and the classic steric impediments provided by neighboring axial methyl groups prevent TEA quenching at the C11 ketone in 2.
60. Wehrli, H.; Heller, M. S.; Schaffner, K.; Jeger, O. Helv. Chim. Acta 1961, 44, 2162-2173. Iriate, J.; Jeger, O. Helv. Chim. Acta 1963, 46, 1599-1609.
61. Wehrli, H.; Heller, M. S.; Schaffner, K.; Jeger, O. Helv. Chim. Acta 1961, 44, 2162-2173. Iriate, J.; Jeger, O. Helv. Chim. Acta 1963, 46, 1599-1609.
62. 23 led to a mixture of three products by glc which we attribute to α-cleavage products. Prolonged photolysis gave a fourth product at a longer retention time than 5 which we believe is the cyclobutanol. None of the fourth product was observable in the absence of added TEA or t-butyl alcohol.
63. Wagner, P. J. J. Am. Chem. Soc. 1967, 89, 5898-5901. Wagner, P. J. Tetrahedron Lett. 1967, 1753-1756. Wagner, P. J. J. Am. Chem. Soc. 1968, 90, 5385-5388.
64. Wagner, P. J. J. Am. Chem. Soc. 1967, 89, 5898-5901. Wagner, P. J. Tetrahedron Lett. 1967, 1753-1756. Wagner, P. J. J. Am. Chem. Soc. 1968, 90, 5385-5388.
65. Wagner, P. J. J. Am. Chem. Soc. 1967, 89, 5898-5901. Wagner, P. J. Tetrahedron Lett. 1967, 1753-1756. Wagner, P. J. J. Am. Chem. Soc. 1968, 90, 5385-5388.
66. Nau, W. M.; Cozens, F. L.; Scaiano, J. C. J. Am. Chem. Soc. 1996, 118, 2275-2282. Nau, W. M.; Cozens, F. L.; Adam, W.; Scaiano, J. C. Book of Abstracts; XVIth IUPAC Symposium on Photochemistry, July 21-26, 1996, Helsinki, Finland, pp 67 and 68.
67. Nau, W. M.; Cozens, F. L.; Scaiano, J. C. J. Am. Chem. Soc. 1996, 118, 2275-2282. Nau, W. M.; Cozens, F. L.; Adam, W.; Scaiano, J. C. Book of Abstracts; XVIth IUPAC Symposium on Photochemistry, July 21-26, 1996, Helsinki, Finland, pp 67 and 68.
68. intraTTET.
69. The Z → E quantum efficiencies reported for compounds 1, 2, and 3 correct and replace those reported in the preliminary communication.