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Typical examples of alkyl radical cyclization onto heteroaromatic rings: (a) Murphy, J. A.; Sherburn, M. S. Tetrahedron 1991, 47, 4077-4088.
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Leading references to cyclization of aryl radicals onto aromatic rings: Clyne, M. A.; Aldaggagh, F. Org. Biomol. Chem. 2006, 4, 268-277.
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For cyclizations of β-dicarbonyl compounds
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For cyclizations of β-dicarbonyl compounds: Snider, B. B. Chem. Rev. 1996, 96, 339-363.
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For methods that do not involve xanthates: a
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For methods that do not involve xanthates: (a) Ishibashi, H.; Nakamura, N.; Ito, K.; Kitayama, S.; Ikeda, M. Heterocycles 1990, 31, 1781-1784.
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For a related approach to cyclization onto a cross-conjugated ketone, see
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For a related approach to cyclization onto a cross-conjugated ketone, see: Villar, F.; Kolly-Kovac, T.; Equey, O.; Renaud, P. Chem.-Eur. J. 2003, 9, 1566-1577.
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0034612966
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For example: a
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For example: (a) Camps, P.; González, A.; Muñoz-Torrero, D.; Simon, M.; Zúñiga, A.; Martins, M. A.; Font-Bardia, M.; Solan, X. Tetrahedron 2000, 56, 8141-8151.
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Oxidation of trimethylsilyl ethers of paraaryl phenols is more efficient and gives yields in the range 66-82, Felpin, F.-X. Tetrahedron Lett. 2007, 48, 409-412. In our hands, the triisopropyl ether of para-propylphenol (cf. ref 11) did not react with PhI(OAc)2
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2.
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Cf.: McKillop, A.; McLaren, L.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1994, 2047-2048.
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Cf.: McKillop, A.; McLaren, L.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1994, 2047-2048.
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Cf.: Pelter, A.; Ward, R. S.; Abd-El-Ghani, A. J. Chem. Soc., Perkin Trans. 1 1992, 2249-2251.
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Cf.: Pelter, A.; Ward, R. S.; Abd-El-Ghani, A. J. Chem. Soc., Perkin Trans. 1 1992, 2249-2251.
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32
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We examined t-BuOOH because a few examples of phenol oxidation in acceptable yield had been reported: (a) Murahashi, S.-I, Naota, T, Miyaguchi, N, Noda, S. J. Am. Chem. Soc. 1996, 118, 2509-2510
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We examined t-BuOOH because a few examples of phenol oxidation in acceptable yield had been reported: (a) Murahashi, S.-I.; Naota, T.; Miyaguchi, N.; Noda, S. J. Am. Chem. Soc. 1996, 118, 2509-2510.
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(b) Ochiai, M.; Nakanishi, A.; Yamada, A. Tetrahedron Lett. 1997, 38, 3927-2930.
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We did not try the recently reported use of oxone it does not appear to give high yields in cases where the alkyl group on the phenol is larger than methyl, Carreño, M. C, González-López, M, Urbano, A. Angew. Chem, Int. Ed. 2006, 45, 2737-2741
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We did not try the recently reported use of oxone (it does not appear to give high yields in cases where the alkyl group on the phenol is larger than methyl): Carreño, M. C.; González-López, M.; Urbano, A. Angew. Chem., Int. Ed. 2006, 45, 2737-2741.
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Wright, S.W.1
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As judged by using bromide 25 as a test case.
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As judged by using bromide 25 as a test case.
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39
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34547425079
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2 alone afforded a complex mixture of products.
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2 alone afforded a complex mixture of products.
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Review on applications of Bi(III) compounds: Leonard, N. M.; Wieland, I. C.; Mohan, R. S. Tetrahedron 2002, 58, 8373-8397.
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Review on applications of Bi(III) compounds: Leonard, N. M.; Wieland, I. C.; Mohan, R. S. Tetrahedron 2002, 58, 8373-8397.
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Examples of 7-exo trigonal cyclization: (a) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051-9052.
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