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(b) Houk, K. N.; Gonzalez, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81-90.
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Houk, K.N.1
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(c) Wiest, O.; Montiel, D. C.; Houk, K. N. J. Phys. Chem. A 1997, 101, 8378-8388.
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Wiest, O.1
Montiel, D.C.2
Houk, K.N.3
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5
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33744750539
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Reviews: a
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Reviews: (a) Fanning, K. N.; Jamieson, A. G.; Sutherland, A. Curr. Org. Chem. 2006, 10, 1007-1020.
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(2006)
Curr. Org. Chem
, vol.10
, pp. 1007-1020
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Fanning, K.N.1
Jamieson, A.G.2
Sutherland, A.3
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8
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4444225192
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(b) Koh, J. H.; Gagné, M. R. Angew. Chem., Int. Ed. 2004, 43, 3459-3461.
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(2004)
Angew. Chem., Int. Ed
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, pp. 3459-3461
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Koh, J.H.1
Gagné, M.R.2
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9
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34848816462
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Although intramolecular trapping of intermediates was described in ref 4b, substituted hexadienes and large ligands unlike any structure described herein were used. Our studies on how these factors affect the mechanism of the Pd(II)-promoted Cope rearrangement will be described in a future report
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(c) Although intramolecular trapping of intermediates was described in ref 4b, substituted hexadienes and large ligands unlike any structure described herein were used. Our studies on how these factors affect the mechanism of the Pd(II)-promoted Cope rearrangement will be described in a future report.
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10
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0033601118
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The Pd(0)-promoted Cope reaction is thought to proceed through a stepwise dissociative mechanism. See: Nakamura, H.; Iwama, H.; Ito, M.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 10850-10851. We will describe calculations on such reactions in a future report.
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The Pd(0)-promoted Cope reaction is thought to proceed through a stepwise dissociative mechanism. See: Nakamura, H.; Iwama, H.; Ito, M.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 10850-10851. We will describe calculations on such reactions in a future report.
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11
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0006111078
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In addition to aryl substitution at C2 of the diene, alkyl substitution at C1, C2, or C3, as well as phenyl or hydroxy substitution at C3 have all been experimentally explored. See, for example: Bluthe, N, Malacria, M, Gore, J. Tetrahedron Lett. 1983, 24, 1157-1160;
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In addition to aryl substitution at C2 of the diene, alkyl substitution at C1, C2, or C3, as well as phenyl or hydroxy substitution at C3 have all been experimentally explored. See, for example: Bluthe, N.; Malacria, M.; Gore, J. Tetrahedron Lett. 1983, 24, 1157-1160;
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13
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0345511748
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Trebellas, J. C.; Olechowski, J. R.; Jonassen, H. B. J. Organomet. Chem. 1966, 6, 412-420.
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(1966)
J. Organomet. Chem
, vol.6
, pp. 412-420
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Trebellas, J.C.1
Olechowski, J.R.2
Jonassen, H.B.3
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14
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34848926505
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Calculations were performed at the B3LYP/LANL2DZ level of theory using Gaussian 03. Free energies at 25°C are reported throughout. See Supporting Information for additional details, including references and comparisons with other levels of theory (which suggest that the results described herein are not very sensitive to the level employed).
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Calculations were performed at the B3LYP/LANL2DZ level of theory using Gaussian 03. Free energies at 25°C are reported throughout. See Supporting Information for additional details, including references and comparisons with other levels of theory (which suggest that the results described herein are not very sensitive to the level employed).
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15
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34848912508
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4a We will describe results that bear on this issue in a future report.
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4a We will describe results that bear on this issue in a future report.
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16
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4243664295
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σ
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σ constants: Hansen, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
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(1991)
Chem. Rev
, vol.91
, pp. 165-195
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constants1
Hansen, C.2
Leo, A.3
Taft, R.W.4
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17
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0346936796
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For leading references, see
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For leading references, see: Olah, G. A.; Berrier, A. L.; Prakash, G. K. S. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 1998-2002.
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(1981)
Proc. Natl. Acad. Sci. U.S.A
, vol.78
, pp. 1998-2002
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Olah, G.A.1
Berrier, A.L.2
Prakash, G.K.S.3
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18
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34848915759
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3 (w/CPCM) resulted in a change of mechanism for both the R = H and R = CN cases from concerted to stepwise, but the well depths for these cases were only 0.1 and 1.1 kcal/mol, respectively. See Supporting Information for additional details.
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3 (w/CPCM) resulted in a change of mechanism for both the R = H and R = CN cases from concerted to stepwise, but the well depths for these cases were only 0.1 and 1.1 kcal/mol, respectively. See Supporting Information for additional details.
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19
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0038701495
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This rearrangement can also be classified as a sigmahaptotropic rearrangement Goldschmidt, Z, Gottlier H. E, Cohen, D. J. Organomet. Chem. 1985, 294, 219-233, since the metal migrates over the allyl fragment to which it is attached as the Cope rearrangement occurs, ending up attached to the newly formed C=C π-bond
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This rearrangement can also be classified as a " sigmahaptotropic" rearrangement (Goldschmidt, Z.; Gottlier H. E.; Cohen, D. J. Organomet. Chem. 1985, 294, 219-233), since the metal migrates over the allyl fragment to which it is attached as the Cope rearrangement occurs, ending up attached to the newly formed C=C π-bond.
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22
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33748225178
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Complexation of Cope transition structures by Li+: Jiao, H.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1760-1763.
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(b) Complexation of Cope transition structures by Li+: Jiao, H.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1760-1763.
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23
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34848922996
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By halogens: Wang. S. C.; Tantillo, D. J. J. Phys. Chem. A, in press.
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By halogens: Wang. S. C.; Tantillo, D. J. J. Phys. Chem. A, in press.
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24
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0347419941
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Transition-state protonation: Hoffmann, R.; Tantillo, D. J. Angew. Chem., Int. Ed. 2003, 42, 5877-5882.
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(c) "Transition-state protonation": Hoffmann, R.; Tantillo, D. J. Angew. Chem., Int. Ed. 2003, 42, 5877-5882.
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25
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33847801098
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Seminal discussions of related concepts: Fukui, K.; Inagaki, S. J. Am. Chem. Soc. 1975, 97, 4445-4452.
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(d) Seminal discussions of related concepts: Fukui, K.; Inagaki, S. J. Am. Chem. Soc. 1975, 97, 4445-4452.
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27
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34848888907
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Note also that the Pd(II) version involves zwitterions rather than diradicals
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Note also that the Pd(II) version involves zwitterions rather than diradicals.
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28
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33746321900
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These intermediates should perhaps be described as para intermediates Northrop, B. H.; O'Malley, D. P.; Zografos, A. L.; Baran, P. S.; Houk, K. N. Angew. Chem., Int. Ed. 2006, 45, 4126-4130.
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(a) These intermediates should perhaps be described as "para intermediates" (Northrop, B. H.; O'Malley, D. P.; Zografos, A. L.; Baran, P. S.; Houk, K. N. Angew. Chem., Int. Ed. 2006, 45, 4126-4130.
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29
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33947296296
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For the related term twixtyl, see:, 92
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For the related term "twixtyl", see: Hoffmann, R.; Swaminathan, S.; Odell, B, G.; Gleiter, R. J. Am. Chem. Soc. 1970, 92, 7091-7097.)
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(1970)
J. Am. Chem. Soc
, pp. 7091-7097
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Hoffmann, R.1
Swaminathan, S.2
Odell, B.G.3
Gleiter, R.4
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30
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0034827199
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and in some cases may reside on calderas (Doering, W. v. E.; Eklmanis, J. L.; Belfield, K. D.; Klärner, F. G.; Krawczyk, B. J. Am. Chem. Soc. 2001, 123, 5532-5541).
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and in some cases may reside on "calderas" (Doering, W. v. E.; Eklmanis, J. L.; Belfield, K. D.; Klärner, F. G.; Krawczyk, B. J. Am. Chem. Soc. 2001, 123, 5532-5541).
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34247531301
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A recent paper describes, for some related [3,3] shifts of heterodienes, intermediates followed by small barriers to form the products: Watson, M. P.; Overman, L. E.; Bergman, R. G. J. Am. Chem. Soc. 2007, 129, 5031-5044.
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(b) A recent paper describes, for some related [3,3] shifts of heterodienes, intermediates followed by small barriers to form the products: Watson, M. P.; Overman, L. E.; Bergman, R. G. J. Am. Chem. Soc. 2007, 129, 5031-5044.
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