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(c) for an excellent review on the PRE see: H. Fischer, Chem. Rev., 2001, 101, 3581-3610.
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For a selection of PRE in organic synthesis see: (c) A. Studer, Chem. Eur. J., 2001, 7, 1159-1164; (d) A. D. Allen, M. F. Fenwick, H. H. Riyad and T. T. Tidwell, J. Org. Chem., 2001, 66, 5759-5765; (e) C. Leroi, B. Fenet, J.-L. Couturier, O. Guerret and M. A. Ciufolini, Org. Lett., 2003, 5, 1079-1081.
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For a selection of PRE in organic synthesis see: (c) A. Studer, Chem. Eur. J., 2001, 7, 1159-1164; (d) A. D. Allen, M. F. Fenwick, H. H. Riyad and T. T. Tidwell, J. Org. Chem., 2001, 66, 5759-5765; (e) C. Leroi, B. Fenet, J.-L. Couturier, O. Guerret and M. A. Ciufolini, Org. Lett., 2003, 5, 1079-1081.
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9
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0141742136
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For a selection of PRE in organic synthesis see: (c) A. Studer, Chem. Eur. J., 2001, 7, 1159-1164; (d) A. D. Allen, M. F. Fenwick, H. H. Riyad and T. T. Tidwell, J. Org. Chem., 2001, 66, 5759-5765; (e) C. Leroi, B. Fenet, J.-L. Couturier, O. Guerret and M. A. Ciufolini, Org. Lett., 2003, 5, 1079-1081.
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0003843752
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(a) S. Z. Zard, Radicals in Organic Synthesis, ed. P. Renaud and M. P. Sibi, Wiley-VCH, Weinheim, 2001, vol. 1, p. 90;
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0001044552
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(a) For the generation of radicals from phenyl selenides and tris (trimethylsilyl)silane-AIBN see: M. Ballestri, C. Chatgilialoglu, K. B. Clark, D. Griller, B. Giese and B. Kopping, J. Org. Chem., 1991, 56, 678-683;
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(d) M. Alajarín, P. Molina, A. Vidal and F. Tovar, Tetrahedron, 1997, 53, 13449-13472;
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(e) M. Alajarín, A. Vidal, F. Tovar, A. Arrieta, B. Lecea and F. P. Cossío, Chem. Eur. J., 1999, 5, 1106-1117;
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2942751784
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note
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The purification by column chromatography of the C-methyl-C-phenyl ketenimines 9e,f must be carried out using a short path of silica gel to avoid their decomposition.
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-
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35
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2942701704
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note
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On the basis of our previous results (Scheme 1), we presumed that the transformations 9 → 10 would also require a stoichiometric amount of the radical initiator, AIBN.
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36
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0001466676
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(a) For other examples of (heteroaryl)methyl radicals see: A. R. Katritzky, B. Yang and N. S. Dalal, J. Org. Chem., 1998, 63, 1467-1472;
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2942746121
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note
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Wako Chemical GmbH, technical specifications.
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39
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2942716616
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note
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For analytical and spectroscopic data of 2-diphenylmethyl-7-methylindole 15 see ref. 5b. The conversion of ketenimine 9b into indole 15 is a reductive process in which the hydrogen atom donor toward the intermediate radical 13b is not obvious. A similar result was found and discussed in ref. 5b.
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