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2942679723
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note
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This experiment was carried out on 2 and not 1 as the appearance of two different species at cold temperature with 1 could result from the dimerization of the pyridone and not from the two atropisomers.
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34
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See Supporting Information
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See Supporting Information.
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0034282470
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36
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2942696711
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note
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The (un)catalyzed aminolysis of PNPCC is fast even in the presence of only one equivalent of propylamine relative to the carbonate. This precludes the use of pseudo-first-order conditions necessary to determine the rate constant of the reaction.
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37
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33847087292
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The pyridone is known to readily self-dimerize in aprotic solvents. Yet, under the very dilute conditions used in our study, the dimerization alone cannot account for the lower catalytic activity of the pyridone over 1. For instance, it was found that 37% of the pyridone exists as a dimer in chloroform for an initial concentration of 2 mM (as compared to 0.04 mM in our case), see: Beak, P.; Covington, J. B.; Smith, S. G.; White, J. M.; Zeigler, J. M. J. Org. Chem. 1980, 45, 1354-1362.
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38
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2942644921
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note
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3CN precludes the accurate determination of the binding constant.
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39
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0345724829
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