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The relative energies (kcal/mol) discussed in the text are enthalpies. DFT ground-state energies for i -Pr- and DIP-based derivatives for compounds shown in Scheme 4 are presented in the Supporting Information
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The relative energies (kcal/mol) discussed in the text are enthalpies. DFT ground-state energies for i -Pr- and DIP-based derivatives for compounds shown in Scheme 4 are presented in the Supporting Information.
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34
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Three-dimensional structures of all calculated compounds are included in the Supporting Information (MOL file format). MOL files can be read by many programs, including the Mercury program freely available at
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Three-dimensional structures of all calculated compounds are included in the Supporting Information (MOL file format). MOL files can be read by many programs, including the Mercury program freely available at http://www.ccdc.cam. ac.uk/products/mercury/.
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35
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0345124573
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There is one example of a structurally characterized six-membered-ring derivative that exists as a bis-imine rather than an imine-enamine. In this case, however, both imine nitrogen atoms bear an unsaturated group (3-pentene-2-thione) that stabilizes the bis-imine form via conjugation: Jensen, H. P.; Kristensen, B. S.; Mosbaek, H.; Søtofte, I. Acta Chem. Scand. 1978, A32, 141-148
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N -methyl mono-imines are calculated to be more stable than the corresponding enamines by 3.0 (five-membered), 1.6 (six-membered), and 0.3 kcal/mol (seven-membered).
-
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37
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79952920731
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1-Methylcycloalkenes are more stable than methylenecycloalkanes by 3.3 (five-membered ring), 7.2 (six-membered ring), and 2.3 kcal/mol (seven-membered ring).
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79952973878
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3-Ph substituents on nitrogen atoms, both trans/trans and trans/cis isomers are observed in the unit cell. (26a)
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3-Ph substituents on nitrogen atoms, both trans/trans and trans/cis isomers are observed in the unit cell. (26a)
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49
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0038678761
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For examples of acyclic bis-imines with σ-trans conformation see
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79952951610
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2v symmetry in solution)
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2v symmetry in solution).
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79952976584
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Structures and energies of various cyclic 1,2-keto-enamines/1,2-keto- imines and 1,2-keto-enol/1,2-diketones are included in the Supporting Information
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Structures and energies of various cyclic 1,2-keto-enamines/1,2-keto- imines and 1,2-keto-enol/1,2-diketones are included in the Supporting Information.
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79952909516
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See the Supporting Information for NMR spectra
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See the Supporting Information for NMR spectra.
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See the Supporting Information for details.
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