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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, 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-La
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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.; 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. gaussian03, Revision B.04, Gaussian, Pittsburgh PA, 2003.
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60249087881
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Müller, N.; Falk, A. Ball and Stick V.3.7.6, Molecular Graphics Application for MacOS Computers, Johannes Kepler University, Linz, 2000.
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Müller, N.; Falk, A. Ball and Stick V.3.7.6, Molecular Graphics Application for MacOS Computers, Johannes Kepler University, Linz, 2000.
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13
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46949089268
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For a recent review on concerted but asynchronous carbocation rearrangements, see:
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For a recent review on concerted but asynchronous carbocation rearrangements, see:. Tantillo D.J. J. Phys. Org. Chem. 21 (2008) 561-570
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(2008)
J. Phys. Org. Chem.
, vol.21
, pp. 561-570
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Tantillo, D.J.1
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14
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60249093153
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2 bridge with two H's) was also located; the computed barrier (not including entropy) for this [4+2] reaction is 10.72 kcal/mol and it is exothermic by 14.87 kcal/mol. See Supplementary data for details.
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2 bridge with two H's) was also located; the computed barrier (not including entropy) for this [4+2] reaction is 10.72 kcal/mol and it is exothermic by 14.87 kcal/mol. See Supplementary data for details.
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15
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33646023740
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* of the protonated carbonyl is observed. The latter sort of interaction has been observed for various other molecules, including natural products; see, for example:
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* of the protonated carbonyl is observed. The latter sort of interaction has been observed for various other molecules, including natural products; see, for example:. McCrindle R., and McAlees A.J. J. Chem. Soc., Chem. Commun. (1983) 61-62
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(1983)
J. Chem. Soc., Chem. Commun.
, pp. 61-62
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McCrindle, R.1
McAlees, A.J.2
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16
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34848889283
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Becker M.H., Chua P., Downham R., Douglas C.J., Garg N.K., Hiebert S., Jaroch S., Matsuoka R.T., Middleton J.A., Ng F.W., and Overman L.E. J. Am. Chem. Soc. 129 (2007) 11987-12002
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(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 11987-12002
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Becker, M.H.1
Chua, P.2
Downham, R.3
Douglas, C.J.4
Garg, N.K.5
Hiebert, S.6
Jaroch, S.7
Matsuoka, R.T.8
Middleton, J.A.9
Ng, F.W.10
Overman, L.E.11
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18
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50149117209
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{A figure is presented}
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Waibel M., and Hasserodt J. J. Org. Chem. 73 (2008) 6119-6126 {A figure is presented}
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(2008)
J. Org. Chem.
, vol.73
, pp. 6119-6126
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Waibel, M.1
Hasserodt, J.2
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19
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60249087976
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note
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A-to-B being less polar than A, but also suggesting that the barrier for this reaction is likely to be low in a variety of environments.
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