Novel radical cation reactions of bichromophoric systems. Transannular aryl migrations; Mechanistic and exploratory organic photochemistry

Journal of Organic Chemistry

Volumn 61, Issue 19, 1996, Pages 6526-6534

  Zimmerman, Howard E ^a   Hoffacker, Kurt D ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001525438     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960467l     Document Type: Article

References (37)

1. This is part 244 of our general series and 181 of our photochemical papers.
2. Photochemical part 179: Zimmerman, H. E.; Kutateladze, A. G. J. Am. Chem. Soc. 1996, 117, 249-250.
3. (a) Zimmerman, H. E.; Grunewald, G. L. J. Am. Chem. Soc. 1966, 88, 183-184.
4. (b) See ref 3c,d for reviews.
5. (c) Zimmerman, H. E. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker, Inc., New York: 1991; Vol. 11.
6. (d) Zimmerman, H. E. In Handbook of Photochemistry and Photobiology; Horspool, W., Song, P. S., Eds.; CRC Press: London, 1995.
7. Zimmerman, H. E.; Mariano, P. S. J. Am. Chem. Soc. 1969, 91, 1718-1727.
8. (a) Kavarnos, G. J.; Turro, N. J. Chem. Rev. 1986, 86, 401-449.
9. (b) Albrecht, E.; Averdung, J.; Bischof, E. W.; Hiedbreder, A.; Kirschberg, T.; Müller, F.; Mattay, J. J. Photochem. Photobiol. A: Chem. 1994, 82, 219-232.
10. (a) Arnold, D. R.; Maroulis, A. J. J. Am. Chem. Soc. 1976, 98, 5931-5937.
11. (b) Mizuno, K.; Ishii, M.; Otsuji, Y. J. Am. Chem. Soc. 1981, 103, 5570-5572.
12. (c) Mattes, S. L.; Farid, S. J. Am. Chem. Soc. 1983, 105, 1387-1389.
13. (d) Mattes, S. L.; Farid, S. J. Am. Chem. Soc. 1986, 108, 7356-7361.
14. Zimmerman, H. E.: Nuss, J. M. J. Org. Chem. 1986, 51, 4604-4617.
15. (a) Mattes, S. L.; Farid, S. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1983; Vol. 6, p 233.
16. (b) Arnold, D. R.; Maroulis, A. J. J. Am. Chem. Soc. 1976, 98, 5931-5937.
17. Gollnick, K.; Schnatterer, A.; Utschick, G. J. Org. Chem. 1993, 58, 6049-6056.
18. Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259-271.
19. Gaussian 94, Revision C.2: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1995.
20. NBO 4.0. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. Theoretical Chemistry Institute, University of Wisconsin, Madison, WI, 1994.
21. Zimmerman, H. E.; Little, R. D. J. Am. Chem. Soc. 1974, 96, 5143-5152.
22. Görner, H. J. Phys. Chem. 1982, 86, 2028-2035.
23. Wagner, P. J.; May, M. L. J. Phys. Chem. 1991, 95, 10317-10321;
24. Dictionary of π-Electron Calculations; Coulson, C. A., Streitwieser, A., Eds.; W. H. Freeman and Co.: San Francisco, 1965.
25. Cf. Zimmerman, H. E.; Rieke, R. D.; Scheffer, J. R. J. Am. Chem. Soc. 1967, 89, 2033-2047.
26. "Stereoselectivity" and "stereospecificity" are used here in the context suggested originally: Zimmerman, H. E.; Singer, L.; Thyagarajan, B. S. J. Am. Chem. Soc. 1959, 81, 108-116.
27. Zimmerman, H. E.; Kutateladze, A. G. J. Org. Chem. 1995, 60, 6008-6009.
28. (a) Allinger, N. L. MM3, University of Georgia, Dec 1990.
29. (b) Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
30. Sodium metavanadate solution was prepared by dissolving the appropriate amount of sodium metavanadate in 5% sodium hydroxide. A 1 cm thick solution of 0.07 M sodium metavanadate cuts off more than 99.9% of the light intensity with wavelengths shorter than 324 nm.
31. Meites, L.; Meites, T. Anal. Chem. 1948, 20, 984-985.
32. Sheldrick, G. M. SHELXTL PLUS, VERSION 4.2, Siemens Analytical X-Ray Instrumentations, Inc., Madison, WI.
33. Sheldrick, G. M. J. Appl. Crystallogr. Manuscript in preparation.
34. Zimmerman, H. E.; Gruenbaum, W. T. J. Org. Chem. 1978, 43, 1997-2005.
35. Babler, J. H.; Haack, R. A. Synth. Commun. 1983, 13, 905-911.
36. Zimmerman, H. E.; Cotter, B. R. J. Am. Chem. Soc. 1974, 96, 7445-7453.
37. The author has deposited atomic coordinates for 17, 22-25, 26a, 27, and 28 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.