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34
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8444227536
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note
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1H NMR investigations of the mechanism of the α-chlorination of cyclohexanone by NCS catalyzed by (1R,2R)-diphenylethylenediamine. These investigations showed that the active catalyst was the condensation product between (1R,2R)-diphenylethylenediamine and cyclohexanone (3h) and not (1R,2R)-diphenylethylenediamine.
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35
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0037195702
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For the first use of 4,5-DPI as an organocatalyst, see: a) N. Halland, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2002, 67, 8331;
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J. Org. Chem.
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Halland, N.1
Hazell, R.G.2
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36
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0013144803
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For other imidazolidine-catalyzed reactions see: b) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2003, 115, 685; Angew. Chem. Int. Ed. 2003, 42, 661;
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Halland, N.1
Aburel, P.S.2
Jørgensen, K.A.3
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37
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0037429423
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For other imidazolidine-catalyzed reactions see: b) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2003, 115, 685; Angew. Chem. Int. Ed. 2003, 42, 661;
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Angew. Chem. Int. Ed.
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38
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0242323633
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c) N. Halland, T. Hansen, K. A. Jørgensen, Angew. Chem. 2003, 115, 4955; Angew. Chem. Int. Ed. 2003, 42, 5105;
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Halland, N.1
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39
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0242323633
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c) N. Halland, T. Hansen, K. A. Jørgensen, Angew. Chem. 2003, 115, 4955; Angew. Chem. Int. Ed. 2003, 42, 5105;
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40
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d) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2004, 116, 1292; Angew. Chem. Int. Ed. 2004, 43, 1272.
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Halland, N.1
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d) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2004, 116, 1292; Angew. Chem. Int. Ed. 2004, 43, 1272.
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42
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6044224571
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For a recent example of rate acceleration of amine-catalyzed reactions by the addition of acids, see: N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420.
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Mase, N.1
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43
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3042625080
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For a recent example of rate acceleration of amine-catalyzed reactions by the addition of acids, see: N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420.
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44
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8444244956
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note
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We believe that acid additives promote enamine formation and suppress chlorination of the catalyst.
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45
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8444239044
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note
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2-Nitrobenzoic acid (20 mol%) led to less than 1% conversion after 18 h in the absence of 4,5-DPI 3i in a 1:1 mixture of cyclohexanone and NCS at ambient temperature.
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46
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8444236098
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note
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Less than 1% conversion of 1e and 1f was observed in the absence of 2-nitrobenzoic acid.
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47
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8444230200
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note
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No racemization was found to occur during filtration through a short silica plug.
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48
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8444227179
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note
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4 were required.
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50
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0345664754
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L. E. Martinez, J. L. Leighton, D. H. Carsten, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5897.
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