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For papers on conformational analysis of o-tert-butylanilide derivatives by other groups, see: a D. P. Curran, G. R. Hale, S. J. Geib, A. Balog, Q. B. Cass, A. L. G. Degani, M. Z. Hemandes, L. C. G Freitas, Tetrahedron: Asymmetry 1997, 8, 3955-3975;
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For papers on conformational analysis of o-tert-butylanilide derivatives by other groups, see: a) D. P. Curran, G. R. Hale, S. J. Geib, A. Balog, Q. B. Cass, A. L. G. Degani, M. Z. Hemandes, L. C. G Freitas, Tetrahedron: Asymmetry 1997, 8, 3955-3975;
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For a preliminary communication of this work, see
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For a preliminary communication of this work, see: N. Ototake, T. Taguchi, O. Kitagawa, Tetrahedron Lett. 2008, 49, 5458-5460.
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0037131449
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It is well known that in secondary amides, Z rotamers are thermody-namically more stable than E rotamers
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Angew. Chem. Int. Ed. 2002, 41, 3854-3857. It is well known that in secondary amides, Z rotamers are thermody-namically more stable than E rotamers.
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a) J. Tsuji, J. Synth. Org. Chem. Jpn. 1999, 57, 1036-1050;
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26
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0037195764
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The allylation of o-tert-butylanilide using a π-allyl-Pd catalyst directly gave an N-allylated product without the formation of an O-allylation product. a O. Kitagawa, M. Kohriyama, T. Taguchi, J. Org. Chem. 2002, 67, 8682-8684;
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The allylation of o-tert-butylanilide using a π-allyl-Pd catalyst directly gave an N-allylated product without the formation of an O-allylation product. a) O. Kitagawa, M. Kohriyama, T. Taguchi, J. Org. Chem. 2002, 67, 8682-8684;
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28
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For typical examples, see: a
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36
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66149113014
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N-Allylanilides 2a-2h in toluene were heated until the changes of E/Z ratios became negligible (reaction time described in Table 5). On the other hand, although thermal isomerization of franyl derivative 2i (E rotamer) was also investigated, the exact equilibrium ratio ((E)-2i/ (Z)-2i) could not be determined, because of the intramolecular Diels-Alder products generated from (Z)-2i.
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N-Allylanilides 2a-2h in toluene were heated until the changes of E/Z ratios became negligible (reaction time described in Table 5). On the other hand, although thermal isomerization of franyl derivative 2i (E rotamer) was also investigated, the exact equilibrium ratio ((E)-2i/ (Z)-2i) could not be determined, because of the intramolecular Diels-Alder products generated from (Z)-2i.
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37
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66149157067
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For typical papers on the E-rotamer preference of N-alkylated anilide derivatives, see: a B. F. Pederson, B. Pederson, Tetrahedron 1956, 2995-3001;
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For typical papers on the E-rotamer preference of N-alkylated anilide derivatives, see: a) B. F. Pederson, B. Pederson, Tetrahedron 1956, 2995-3001;
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38
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0024460631
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b) A. Itai, Y. Toriumi, N. Tomioka, H. Kagechika, I. Azumaya, K. Shudo, Tetrahedron Lett. 1989, 30, 6177-6180;
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40
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33751156319
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The E-rotamer preference of N-methylanilides has been rationalized on the basis of such an n-π interaction: S. Saito, Y. Toriumi, N. Tomioka, A. Itai, J. Org. Chem. 1995, 60, 4715-4720.
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The E-rotamer preference of N-methylanilides has been rationalized on the basis of such an n-π interaction: S. Saito, Y. Toriumi, N. Tomioka, A. Itai, J. Org. Chem. 1995, 60, 4715-4720.
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41
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84893169025
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All calculations were carried out by using the GAMESS (US) package: M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. Su, T. L. Windus, M. Dupuis, J. A. Montgomery, J. Comput. Chem. 1993, 14, 1347-1363.
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All calculations were carried out by using the GAMESS (US) package: M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. Su, T. L. Windus, M. Dupuis, J. A. Montgomery, J. Comput. Chem. 1993, 14, 1347-1363.
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42
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66149113411
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CCDC 713422 ((E)-2d) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam. ac.uk/data-request/cif.
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CCDC 713422 ((E)-2d) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam. ac.uk/data-request/cif.
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