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For reviews of organoiodanes, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Koser, G. F. The Chemistry of Functional Groups, Supplemented D; Wiley: New York, 1983; Chapter 18. (c) Varvoglis, A. Synthesis 1984, 709. (d) Ochiai, M.; Nagao, Y. J. Synth. Org. Chem., Jpn. 1986, 44, 660. (e) Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244. (f) Merkushev, E. B. Russ. Chem. Rev. 1987, 56, 826. (g) Ochiai, M. Revs. Heteroatom Chem. 1989, 2, 92. (h) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (i) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett. 1990, 365. (j) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (k) Varvoglis, A. The Chemistry of Polycoordinated Iodine. VHC Publishers: New York, 1992. (l) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21.
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Moss and Zhang also reported a synthesis of the peroxyiodane 1a involving a ligand exchange of a labile (phosphoryloxy)iodane, prepared in situ by the reaction of 1-chloro-1,2-benziodoxol-3(1H)-one with silver diphenyl phosphate in DMSO, with tert-butyl hydroperoxide. See: Moss, R. A.; Zhang, H. J. Am. Chem. Soc. 1994, 116, 4471.
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3, which could scavenge the hydrogen bromide produced in the reactions. For this bromination, both the trichloromethyl radical and the bromine atom, generated from hydrogen bromide, have been suggested to participate in benzylic hydrogen atom abstraction. See: (a) Tanner, D. D.; Arhart, R. J.; Blackburn, E. V.; Das, N. C.; Wada, N. J. Am. Chem. Soc. 1974, 96, 829. (b) Tanner, D. D.; Wada, N. J. Am. Chem. Soc. 1975, 97, 2190. (c) Krosley, K. W.; Gleicher, G. J. J. Org. Chem. 1990, 55, 4469.
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3, which could scavenge the hydrogen bromide produced in the reactions. For this bromination, both the trichloromethyl radical and the bromine atom, generated from hydrogen bromide, have been suggested to participate in benzylic hydrogen atom abstraction. See: (a) Tanner, D. D.; Arhart, R. J.; Blackburn, E. V.; Das, N. C.; Wada, N. J. Am. Chem. Soc. 1974, 96, 829. (b) Tanner, D. D.; Wada, N. J. Am. Chem. Soc. 1975, 97, 2190. (c) Krosley, K. W.; Gleicher, G. J. J. Org. Chem. 1990, 55, 4469.
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It is not at all clear whether or not the added p-methoxyphenol traps radicals generated in the reaction. We found that oxidation of phenols with the peroxyiodane 1a takes place, and the results will be reported elsewhere.
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Furthermore, added galvinoxyl completely inhibits the oxidation of the allyl ether 6a.
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On the other hand, the cyclization rate constants of 1-methoxy-5-hexenyl radicals have been shown to be nearly equal to those for related alkyl radicals lacking the methoxy group. See: (a) Johnson, C. C.; Horner, J. H.; Tronche, C.; Newcomb, M. J. Am. Chem. Soc. 1995, 117, 1684. (b) Newcomb, M.; Filipkowski, M. A.; Johnson, C. C. Tetrahedron Lett. 1995, 36, 3643.
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46 have been generally accepted.
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Photoelectron spectroscopy shows that the oxidation potential of aromatic π electrons of benzyl ethers is lower than that of the nonbonding electrons on oxygen. Therefore, the charge density of benzyl ether cation radicals has been assumed to be located in the π system rather than localized on the potentially oxidizable oxygen atom. See: (a) Mayeda, E. A.; Miller, L. L.; Wolf, J. F. J. Am. Chem. Soc. 1972, 94, 6812. (b) Pincock, J. A.; Pincock, A. L.; Fox, M. A. Tetrahedron 1985, 41, 4107.
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Photoelectron spectroscopy shows that the oxidation potential of aromatic π electrons of benzyl ethers is lower than that of the nonbonding electrons on oxygen. Therefore, the charge density of benzyl ether cation radicals has been assumed to be located in the π system rather than localized on the potentially oxidizable oxygen atom. See: (a) Mayeda, E. A.; Miller, L. L.; Wolf, J. F. J. Am. Chem. Soc. 1972, 94, 6812. (b) Pincock, J. A.; Pincock, A. L.; Fox, M. A. Tetrahedron 1985, 41, 4107.
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