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Replacement of the experimentally used n-propyl group with a methyl group in the calculations should still provide an accurate indication of the relative energies of the various conformations, since the energy differences mainly arise from (1) strain between the vinyl protons and the gem-dimethyl groups (GS1 versus GS2) and (2) differing ring stabilities (GS2 versus GS3). Truncating the alkyl chain by two carbons reduces the number of possible conformations 9-fold and makes the computational study feasible.
-
Replacement of the experimentally used n-propyl group with a methyl group in the calculations should still provide an accurate indication of the relative energies of the various conformations, since the energy differences mainly arise from (1) strain between the vinyl protons and the gem-dimethyl groups (GS1 versus GS2) and (2) differing ring stabilities (GS2 versus GS3). Truncating the alkyl chain by two carbons reduces the number of possible conformations 9-fold and makes the computational study feasible.
-
-
-
-
87
-
-
64549126056
-
-
All calculations were carried out for the gas phase using the Gaussian 03 suite of programs: Frisch, M. J. Gaussian 03, rev. C02; Gaussian Inc.: Wallingford, CT, 2004. See Supporting Information for full reference.
-
All calculations were carried out for the gas phase using the Gaussian 03 suite of programs: Frisch, M. J. Gaussian 03, rev. C02; Gaussian Inc.: Wallingford, CT, 2004. See Supporting Information for full reference.
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-
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-
88
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64549123062
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-
Hodgson, D. M.; Bray, C. D.; Kindon, N. D. Org. Lett. 2005, 7, 6870-6871.
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(2005)
Org. Lett
, vol.7
, pp. 6870-6871
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Hodgson, D.M.1
Bray, C.D.2
Kindon, N.D.3
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90
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-
20444471536
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-
For a recent example of this problem in synthesis, see
-
For a recent example of this problem in synthesis, see: Hodgson, D. M.; Galano, J.-M. Org. Lett. 2005, 7, 2221-2224.
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(2005)
Org. Lett
, vol.7
, pp. 2221-2224
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Hodgson, D.M.1
Galano, J.-M.2
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92
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33748994796
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See also
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See also Beilanger, G.; Dorei, D.; Meinard, F.; Darsigny, V. J. Org. Chem. 2006, 71, 7481-7484.
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(2006)
J. Org. Chem
, vol.71
, pp. 7481-7484
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Beilanger, G.1
Dorei, D.2
Meinard, F.3
Darsigny, V.4
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93
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1642547131
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For a one-pot procedure, see
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For a one-pot procedure, see: Ho, T.-L.; Wong, C. M. Synth. Commun. 1974, 4, 147-149.
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(1974)
Synth. Commun
, vol.4
, pp. 147-149
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-
Ho, T.-L.1
Wong, C.M.2
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94
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57549112579
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For a recent asymmetric development of this process, see
-
For a recent asymmetric development of this process, see: Hodgson, D. M.; Kaka, N. S. Angew. Chem., Int. Ed. 2008, 47, 9958-9960.
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(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 9958-9960
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Hodgson, D.M.1
Kaka, N.S.2
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