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33847604189
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THF depresses the yields, since it is a considerably better hydrogen donor
-
THF depresses the yields, since it is a considerably better hydrogen donor.
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54
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0033591171
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Similar observations have been made for similar systems: P. I. Dalko, Tetrahedron Lett. 1999, 40, 4035-4036.
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0001874030
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For the preparation, see: [20a] M. Schmittel, M. Levis, Synlett 1996, 315-316. - For use as SET oxidant, see:
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The corresponding alcohol 10c was prepared by Wittig reaction in analogy to: D. A. Frey, S. H. K. Reddy, K. D. Moeller, J. Org. Chem. 1999, 64, 2805-2813. The mesylate was prepared by deprotonation of the alcohol with 1.1 equiv. of BuLi (1.6 M in hexane) and addition of 1.1. equiv. of MsCl at -78°C in THF.
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33847574501
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note
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The propensity of benzylic nitroxides to undergo reversible thermal homolysis is well established and used in controlled radical polymerization.
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64
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33947093954
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A. P. Krapcho, J. F. Weimaster, J. M. Eldridge, E. G. E. Jahngen Jr., A. J. Lovey, W. P. Stephens, J. Org. Chem. 1978, 43, 138-147.
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On the reversibility of malonyl radical cyclizations, see: D. P. Curran, J. Sisko, A. Balog, N. Sonoda, K. Naaahara, I. Ryu, J. Chem. Soc., Perkin Trans. 1 1998, 1591-1593.
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For investigations on alkyl radical additions to 1 or 9, see: E. Baciocchi, B. Floris, E. Muraglia, J. Org. Chem. 1993, 58, 2013-2016 and references therein.
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Angew. Chem. Int. Ed. 2000, 39, 1108-1111 and ref. therein.
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76
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33847585382
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-
note
-
In all experiments, where disproportionation to 18/19 was observed, the alkene/alkane ratio was 1:1. It is thus reasonable to use this expression to calculate the ratio of SET oxidation/radical termination in this way.
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77
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0001651317
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0001167956
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(Ed.: J. K. Kochi), Wiley, New York
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81
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33847599595
-
-
note
-
Full details of the crystal determination (except structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-149761 (14a), -149762 (20b), and -149763 (31d). Copies of the data can be obtained free of charge on applicaton to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) + 44-1223/ 336-033; E-mail: deposit@ccdc.cam.ac.uk].
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