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2 can oxidize unactivated alcohol when it is performed in the presence of Wittig reagent; see: L. Blackburn, X. Wei, R. J. K. Taylor, Chem. Commun. 1999, 1337-1338.
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For the oxidation of alcohols, see: M. Frigerio, M. Santagostino, S. Sputore, G. Palmisano, J. Org. Chem. 1995, 60, 7272-7276.
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For other applications of IBX, see: a) K. C. Nicolaou, Y. L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639;
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b) K. C. Nicolaou, P. S. Baran, R. Kranich, Y. L. Zhong, K. Sugita, N. Zou, Angew. Chem. 2001, 113, 208-212;
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23
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28844474319
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For tandem oxidation/Wittig reactions initiated by Dess-Martin periodinane (DMP) or IBX, see: a) C. C. Huang, J. Labelled Compd. Radiopharm. 1987, 24, 676-681;
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27
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0033546262
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IBX used in this study was synthesized according to M. Frigerio, M. Santagostino, S. Sputore, J. Org. Chem. 1999, 64, 4537-4538;
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28
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0002380120
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Caution! IBX, like other hypervalent iodine oxidants, can explode on impact or heating; see: J. B. Plumb, D. J. Harper, Chem. Eng. News 1990, 68(29), 3-3.
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33746212468
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see references [9b] and [11]
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IBX is able to oxidize THF at elevated temperatures (80°C and above); see references [9b] and [11].
-
-
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31
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33746212475
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note
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Oxidation of 5i with IBX (in THF or DMSO) or under Swern conditions led only to the decomposition of the starting material.
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32
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For a few diastereoselective P-3CRs, see: a) S. Marcaccini, D. Miguel, T. Torroba, M. Garcia-Valverde, J. Org. Chem. 2003, 68, 3315-3318;
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38
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33746188803
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note
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13C NMR spectra of 1a-1u are provided in the Supporting Information.
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