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1
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33845400624
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Undergraduate Research Participant, 2004-2006
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Undergraduate Research Participant, 2004-2006.
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2
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0035917348
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R. A. Bunce, D. M. Herron, L. B. Johnson and S. V. Kotturi. J. Org. Chem., 66, 2822 (2001).
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(2001)
J. Org. Chem.
, vol.66
, pp. 2822
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Bunce, R.A.1
Herron, D.M.2
Johnson, L.B.3
Kotturi, S.V.4
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3
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0000583694
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see
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[3a] The pyrrolidine ring is estimated to have 6.5 kcal/mole of strain energy relative to piperidine, see K. B. Wiberg, D. Y. Najaki, and K. M. Morgan, J. Am. Chem. Soc., 115, 3527 (1993);
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(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 3527
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Wiberg, K.B.1
Najaki, D.Y.2
Morgan, K.M.3
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4
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0000608105
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[b] J. D. Cox, Tetrahedron, 19, 1175 (1963).
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(1963)
Tetrahedron
, vol.19
, pp. 1175
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Cox, J.D.1
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5
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0020617257
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[4a] Y. Ito, E. Nakajo, M. Nakatsuka and T. Saegusa, Tetrahedron Lett., 24, 2881 (1983);
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(1983)
Tetrahedron Lett.
, vol.24
, pp. 2881
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Ito, Y.1
Nakajo, E.2
Nakatsuka, M.3
Saegusa, T.4
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7
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0034693113
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see
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A second synthesis proceeded through the same hexahydropyrrolo[1,2-a] quinoline intermediate, see W. H. Pearson and W. Fang, J. Org. Chem., 65, 7158 (2000).
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(2000)
J. Org. Chem.
, vol.65
, pp. 7158
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Pearson, W.H.1
Fang, W.2
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9
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0141853186
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[7a] For cyclization promoted by nickel(0); R. Omar-Amrani, A. Thomas, E. Brenner, R. Schneider and Y. Fort, Org. Lett., 5, 2311 (2003);
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(2003)
Org. Lett.
, vol.5
, pp. 2311
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Omar-Amrani, R.1
Thomas, A.2
Brenner, E.3
Schneider, R.4
Fort, Y.5
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13
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0000272922
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T. Hudlicky, B. C. Ranu, S. M. Naqvi and A. Srnak, J. Org. Chem., 50, 123 (1985).
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(1985)
J. Org. Chem.
, vol.50
, pp. 123
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Hudlicky, T.1
Ranu, B.C.2
Naqvi, S.M.3
Srnak, A.4
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14
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33845398004
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note
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The modest mass balances (ca. 70%) for the reductive cyclizations result from loss of material during chromatography.
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15
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33845402471
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note
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Decarbonylation could also occur before the initial ring closure.
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17
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0000423165
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I. Wender and P. Pino, Eds.; Wiley-Interscience: New York
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[b] J. Tsuji in "Organic Synthesis via Metal Carbonyls," I. Wender and P. Pino, Eds.; Wiley-Interscience: New York, 1977; pp 595-654;
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(1977)
Organic Synthesis Via Metal Carbonyls
, pp. 595-654
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Tsuji, J.1
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18
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0040860518
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M.-A. Pearsall, A. M. Rosan, J. S. Conrad, C. A. Hendrickson, A. L. Pacchia and D. J. Schantz, J. Chem. Educ., 72, A29 (1995).
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(1995)
J. Chem. Educ.
, vol.72
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Pearsall, M.-A.1
Rosan, A.M.2
Conrad, J.S.3
Hendrickson, C.A.4
Pacchia, A.L.5
Schantz, D.J.6
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19
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0002694246
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see
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For a mechanistic discussion of this process, see J. Tsuji and K. Ohno, J. Am. Chem. Soc., 90, 94 (1968).
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(1968)
J. Am. Chem. Soc.
, vol.90
, pp. 94
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Tsuji, J.1
Ohno, K.2
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20
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33845380612
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see ref 8, pp 16-17, 318 and 385
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Poisoning of the catalyst surface by the tetrahydroquinoline products may play a role in deactivating the platinum catalysts, see ref 8, pp 16-17, 318 and 385.
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21
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33845394531
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note
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2 = 0.0957 (all data). CCDC 290046 contains the supplementary crystallographic data for 9. These data can be obtained free of charge from the CCDC at www.cede.cam.ac.uk/data_request/cif.
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27
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0042041206
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Molecular mechanics (UFF) and density functional theory (DFT) calculations on optimized structures of the equatorial methyl and axial methyl isomers did not indicate a clear enthalpic preference for either isomer. UFF calculations [A. K. Rappé, C. J. Casewit, K. S. Colwell, W. A. Goddard, III and W. M. Skiff, J. Am. Chem. Soc., 114, 10024 (1992)] favored equatorial methyl by 1.47 kcal/mole, while DFT calculations favored axial methyl by 2.61 kcal/mole.
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(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 10024
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Rappé, A.K.1
Casewit, C.J.2
Colwell, K.S.3
Goddard III, W.A.4
Skiff, W.M.5
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28
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0038626673
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Gaussian, Inc., Pittsburgh, PA
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DFT calculations were performed using the GAUSSIAN 03 package [M. J. Frisch, et al., Gaussian 03, Gaussian, Inc., Pittsburgh, PA (2004)] at the B3LYP/6-31G** level of theory with full vibrational analysis to derive the thermochemical results.
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(2004)
Gaussian 03
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Frisch, M.J.1
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29
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33845384982
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see ref 17d, p 140
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3 and OH groups, see ref 17d, p 140.
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