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For reviews, see. (a) Leigh, W. J.; Srinivasan, R. Acc. Chem. Res. 1987, 20, 107.
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Padwa, A, Ed, Marcel Dekker: New York
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(b) Hixson, S. S. Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1979; Vol. 4, pp 218-260.
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(b) Srinivasan, R.; Ors, J. A.; Baum, T. J. Org. Chem. 1981, 46, 1950.
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(c) Srinivasan, R.; Baum, T.; Ors, J. A. Tetrahedron Lett. 1981, 22, 4795.
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(a) Srinivasan, R.; Ors, J. A.; Brown, K. H.; Baum, T.; White, L. S.; Rossi, A. R. J. Am. Chem. Soc. 1980,102,5297.
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(b) Srinivasan, R.; Baum, T.; Brown, K. H.; Ors, J. A.; White, L. S.; Rossi, A. R.; Epling, G. A. J. Chem. Soc., Chem. Commun. 1981, 973.
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Epling, G.A.7
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12
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62149141822
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For instance, as pointed out by the same authors, according to deuterium-labeling studies, the dominant photoproduct, cis-1,3,6-heptatriene, is formed via formal electrocyclic [2π, 2ω, 2σ] ring opening of the bicyclo[4,1,0]hept-2-ene ring system in a manner analogous to the 1,3-cyclohexadiene/Ixsx,3,5-hexatriene interconversion; see ref 6
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For instance, as pointed out by the same authors, according to deuterium-labeling studies, the dominant photoproduct, cis-1,3,6-heptatriene, is formed via formal electrocyclic [2π + 2ω + 2σ] ring opening of the bicyclo[4,1,0]hept-2-ene ring system in a manner analogous to the 1,3-cyclohexadiene/Ixsx,3,5-hexatriene interconversion; see ref 6.
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(d) Bernardi, F.; Olivucci, M.; Robb, M. A. J. Photochem. Photobiol, A 1997, 105, 365.
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Bernardi, F.1
Olivucci, M.2
Robb, M.A.3
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19
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62149126720
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Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Montgomery J. A, Jr, Vreven, T, Kudin, K. N, Burant, J. C, Millam, J. M, Iyengar, S. S, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, G. A, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Klene, M, Li, X, Knox, J. E, Hratchian, H. P, Cross, J. B, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth, G. A, Salvador, P, Dannenberg, J. J, Zakrzewski, V. G, Dapprich, S, Daniels, A. D, Strain, M. C, Farkas, O, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Ortiz, J. V, Cui, Q, Baboul, A. G, Clifford, S, Cioslowski, J, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Martin, R. L, Fox, D. J, Keith
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Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03; Gaussian, Inc.: Wallingford, CT, 2004.
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Because the excited electron occupies the antibonding orbital, this can make a longer bond distance. Also see:, Academic Press: New York
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Because the excited electron occupies the antibonding orbital, this can make a longer bond distance. Also see: Jorgensen, W. L.; Salem, L. The Organic Chemist's Book of Orbitals; Academic Press: New York, 1973.
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(1973)
The Organic Chemist's Book of Orbitals
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Jorgensen, W.L.1
Salem, L.2
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