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Oxidation of tetracyanoethylene with iodosylbenzene affords tetracyanoethylene oxide. This reaction probably involves a nucleophilic attack of the oxygen atom of iodosylbenzene to the electron-deficient olefin. See: Moriarty, R. M.; Gupta, S. C.; Hu, H.; Berenschot, D. R.; White, K. B. J. Am. Chem. Soc. 1981, 103, 686.
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Reaction of (diacetoxyiodo)benzene with hydroxide anion produces iodosylbenzene. See: Saltzman, H.; Sharefkin, J. G. Org. Synth. 1963, 43, 60.
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0042483547
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note
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3: C, 54.65; H, 7.98; N, 2.77. Found: C, 54.26; H, 7.95; N, 2.75.
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25
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37049047413
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For syntheses of sodium, calcium, and ammonium 2-iodosylbenzoates, which show low solubility toward common organic solvents, see: (a) Baker, G. P.; Mann, F. G.; Sheppard, N.; Tetlow, A. J. J. Chem. Soc. 1965, 3721.
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(d) Moss, R. A.; Wilk, B.; Krogh-Jespersen, K.; Blair, J. T.; Westbrook, J. D. J. Am. Chem. Soc. 1989, 111, 250.
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37049070576
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For X-ray structure analysis of sodium 2-iodosylbenzoates, see: Katritzky, A. R.; Savage, G. P.; Palenik, G. J.; Qian, K.; Zhang, Z. J. Chem. Soc., Perkin Trans. 2 1990, 1657.
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30
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0042984340
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note
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The recovered diketone 3a in this epoxidation always consists of a mixture of (E)-and (Z)-isomers.
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31
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0000623003
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Moss, R. A.; Alwis, K. W.; Shin, J. J. Am. Chem. Soc. 1984, 106, 2651.
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3-iodane 2 exhibits a modest α-effect. (a) Moss, R. A.; Swamp, S.; Ganguli, S. J. Chem. Soc., Chem. Commun. 1987, 860.
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35
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85088005600
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note
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3-phenyliodanyl group shows a very high leaving group ability and is called a hyperleaving group. See ref 1o.
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