Competitive 1,2- and 1,5-hydrogen shifts following 2-vinylbiphenyl photocyclization

Journal of Organic Chemistry

Volumn 70, Issue 25, 2005, Pages 10447-10452

  Lewis, Frederick D ^a   Sajimon, Meledathu C ^a   Zuo, Xiaobing ^b   Rubin, Michael ^c,d   Gevorgyan, Vladimir ^c  

^a NORTHWESTERN UNIVERSITY   (United States)

^b ARGONNE NATIONAL LABORATORY   (United States)

^c UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^d UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL METHODS; DERIVATIVES; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE; POTENTIAL ENERGY; THERMAL EFFECTS;

HYDROGEN SHIFTS; PHOTOCYCLIZATION; PRODUCT-FORMING PATHWAY; TWO-STEP MECHANISM;

HYDROGEN;

2 VINYLBIPHENYL DERIVATIVE; BIPHENYL DERIVATIVE; DEUTERIUM; HYDROGEN; PHENANTHRENE DERIVATIVE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ISOTOPE LABELING; PHOTOCHEMISTRY; PHOTOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE;

EID: 28744455778     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051730y     Document Type: Article

References (31)

1. Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Verlag Chemie: Weinheim, 1970.
2. De Dobbelaere, J. R.; Van Zeeventer, E. L.; De Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241-244.
3. Roth, W. R. Tetrahedron Lett. 1964, 1009-1013.
4. Hess, B. A.; Baldwin, J. E. J. Org. Chem. 2002, 67, 6025-6033.
5. Alabugin, I. V.; Manoharan, M.; Breiner, B.; Lewis, F. D. J. Am. Chem. Soc. 2003, 125, 9329-9342.
6. Lewis, F. D.; Zuo, X.; Gevorgyan, V.; Rubin, M. J. Am. Chem. Soc. 2002, 124, 13664-13665.
7. Lewis, F. D.; Zuo, X. Photochem. Photobiol. Sci. 2003, 2, 1059-1066.
8. Horgan, S. W.; Morgan, D. D.; Orchin, M. J. Org. Chem. 1973, 38, 3801-3803.
9. Zuo, X. Ph.D. Thesis, Northwestern University, 2002.
10. Gevorgyan, V.; Tando, K.; Uchiyama, N.; Yamamoto, Y. J. Org. Chem. 1998, 63, 7022-7025.
11. Former de Violet, P.; Bonneau, R.; Lapouyade, R.; Koussini, R.; Ware, W. R. J. Am. Chem. Soc. 1978, 100, 6683-6687.
12. Sajimon, M. C.; Lewis, F. D. Photochem. Photobiol. Sci. 2005, 4, 789-791.
13. Harvey, R. G.; Fu, P. P.; Rabideau, P. W. J. Org. Chem. 1976, 41, 3722-3725.
14. Rodríguez, D.; Navarro-Vazquez, A.; Castedo, L.; Dominguez, D.; Saá, C. J. Org. Chem. 2003, 68, 1938-1946.
15. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Gui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A., Gaussian 98, Revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
16. The length of the bond being broken is reported first. Leffler, J. E. Science 1953, 117, 340-341.
17. Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334-338.
18. Isaacs, N. S. Physical Organic Chemistry; 2nd ed.; Longman: Essex, England, 1995.
19. Kamal de Fonseka, K.; Manning, C.; McCullough, J. J.; Yarwood, A. J. J. Am. Chem. Soc. 1977, 99, 8257-8261. ()
20. McCullough, J. J. Acc. Chem. Res. 1980, 13, 270-276.
21. Grellmann, K. H.; Schmitt, U.; Weller, H. Chem. Phys. Lett. 1982, 88, 40-45.
22. Peters, K. S.; Kim, G. J. Phys. Org. Chem. 2005, 18, 1-8. ()
23. Lee, S.; Haynes, J. T. Chim. Phys. 1996, 93, 1783-1807.
24. Klessinger, M.; Michl, J. Excited States and Photochemistry of Organic Molecules; VCH Publishers: New York, 1995.
25. Turro, N. J.; McVey, J.; Ramamurthy, V.; Lechtken, P. Angew. Chem., Int. Ed. Engl. 1979, 18, 572-586.
26. Lewis, F. D.; Crompton, E. M.; Sajimon, M. C.; Gevorgyan, V.; Rubin, M. Photochem. Photobiol. 2005, ASAP.
27. Shah, B. K.; Rodgers, M. A. J.; Neckers, D. C. J. Phys. Chem. A 2004, 108, 5926-5931.
28. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
29. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
30. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
31. Peng, C.; Schlegel, H. B. Isr. J. Chem. 1993, 33, 449-454.