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29
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27644523792
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note
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13C NMR spectrum, a peak at δ = 133.9 ppm could be assigned as the α carbon of the enamine.
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30
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27644552378
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note
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The types of argon available in our institute are "Arcal 1" and "Nertal" (Air Liquide), normally used for arc welding and plasma cutting applications.
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Pitacco, G.1
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32
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27644562385
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note
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13C NMR analysis. Therefore, their formation cannot be explained by oxidation during column chromatography.
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33
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0001592583
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0003675478
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It has been established that five-membered ring cyclic enamines are generally more basic and more reactive towards electrophiles than their six-membered homologues: a) A. G. Cook, M. L. Absi, V. K. Bowden, J. Org. Chem. 1995, 60, 3169-3171;
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0038509986
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b) B. Kempf, N. Hampel, A. R. Ofial, H. Mayr, Chem. Eur. J. 2003, 9, 2209-2218. It should be noted, however, that unlike our intermediates, the cyclic enamines studied in these references do not include the nitrogen atom in the same ring as the carbon-carbon double bond.
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Kempf, B.1
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0842341771
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AM1 calculations (M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909) were performed with the MOPAC 97 program (Fujitsu Limited: 1993-1997) in the CS Chem. 3D® Pro system (CambridgeSoft Corporation, Cambridge, U. S. A.).
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37
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27644522940
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note
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1H NMR spectra is shown in the supporting information; for supporting information see also the footnote on the first page of this article
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39
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27644551555
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note
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Only a trace amount of acid would be sufficient since a proton is released after the cyclisation during the re-aromatisation step.
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40
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27644546864
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(Eds.: Sir D. Barton, W. D. Ollis), Pergamon, Oxford
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a of the phenol can be estimated at about 10: a) D. A. Whiting, in: Comprehensive Organic Chemistry; The Synthesis and Reactions of Organic Compounds, (Eds.: Sir D. Barton, W. D. Ollis), Pergamon, Oxford, 1979, vol. 1, pp. 709-710.
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Whiting, D.A.1
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19744371760
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a of the cyclic iminium ion should lie in the range 10-12; b) R. L. Hinman, Tetrahedron 1968, 24, 185-190.
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0001023594
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b) K. Narayanan, L. Schindler, J. M. Cook, J. Org. Chem. 1991, 56, 359-365.
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48
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27644497309
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note
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[4].
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-
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49
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27644595830
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note
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Experimental details about the preparation of this compound can be found in the supporting information.
-
-
-
-
50
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27644459175
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note
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The structure and characterisation of this compound can be found in the supporting information.
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-
-
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51
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27644452811
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CCDC-273312, -273313, and -273314 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.
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