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11
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0242561589
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note
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In the case of amine tether, both the ene-like and the (3+2) products were obtained.5
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12
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0032555404
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For other ene-like reactions, see: (a) Takahashi, T.; Hirose, Y.; Iwamoto, H.; Doi, T. J. Org. Chem. 1998, 63, 5742.
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0001453658
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(b) Jin, J.; Smith, D. T.; Weinreb, S. M. J. Org. Chem. 1995, 60, 5366. A [4+4] ene reaction with dienes as enophiles was reported, see:
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Jin, J.1
Smith, D.T.2
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84985521805
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(c) Takacs, J. M.; Anderson, L. G.; Madhavan, G. V. B.; Seely, F. L. Angew. Chem. Int. Ed. Engl. 1987, 26, 1013.
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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.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; 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. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
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Trucks, G.W.2
Schlegel, H.B.3
Scuseria, G.E.4
Robb, M.A.5
Cheeseman, J.R.6
Zakrzewski, V.G.7
Montgomery J.A., Jr.8
Stratmann, R.E.9
Burant, J.C.10
Dapprich, S.11
Millam, J.M.12
Daniels, A.D.13
Kudin, K.N.14
Strain, M.C.15
Farkas, O.16
Tomasi, J.17
Barone, V.18
Cossi, M.19
Cammi, R.20
Mennucci, B.21
Pomelli, C.22
Adamo, C.23
Clifford, S.24
Ochterski, J.25
Petersson, G.A.26
Ayala, P.Y.27
Cui, Q.28
Morokuma, K.29
Malick, D.K.30
Rabuck, A.D.31
Raghavachari, K.32
Foresman, J.B.33
Cioslowski, J.34
Ortiz, J.V.35
Baboul, A.G.36
Stefanov, B.B.37
Liu, G.38
Liashenko, A.39
Piskorz, P.40
Komaromi, I.41
Gomperts, R.42
Martin, R.L.43
Fox, D.J.44
Keith, T.45
Al-Laham, M.A.46
Peng, C.Y.47
Nanayakkara, A.48
Gonzalez, C.49
Challacombe, M.50
Gill, P.M.W.51
Johnson, B.G.52
Chen, W.53
Wong, M.W.54
Andres, J.L.55
Head-Gordon, M.56
Replogle, E.S.57
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more..
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17
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0345491105
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Lee, C.1
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23
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(a) Yamaguchi, K.; Jensen, F.; Houk, K. N. Chem. Phys. Lett. 1988, 149, 537.
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Goldstein, E.1
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29
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0242477773
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note
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In addition to TS9, there is another approach for the (3+2) path involving addition of C1 to C5 and O to C6. This path can be ruled out according to Bredt's rule.17 No transition state for this path could be located computationally.
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31
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0000177907
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Another possible path to form the (3+2) product is through the isomerization of 5 to 10. This is similar to the isomerizations of vinylcyclopropanes to cyclopentenes. We could not locate such a transition state, suggesting this path is not possible. For reviews of the isomerizations of vinylcyclopropanes to cyclopentenes, see: (a) Baldwin, J. E. J. Comput. Chem. 1998, 19, 222.
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Baldwin, J.E.1
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33
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0242394404
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note
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Computational evidence to support this argument is that the retro-ene reactions shown below have lower activation energies when R is an electron-donating group as compared to the case when R is an electron-withdrawing group. When R is a good π-electron-withdrawing group, such as CHO, the acidity of the (R-)C-H is increased and the corresponding transition state TS27 is only 16.9 kcal/mol higher than 26.
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35
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0000997465
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For discussions of entropy overestimation in bimolecular reactions in aqueous solution, see: (a) Strajbl, M.; Sham, Y. Y.; Villa, J. V.; Chu, Y. Y.; Warshel, A. J. Phys. Chem. B 2000, 104, 4578.
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J. Phys. Chem. B
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Strajbl, M.1
Sham, Y.Y.2
Villa, J.V.3
Chu, Y.Y.4
Warshel, A.5
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