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6 in 10 min were observed by NMR to undergo acid-catalyzed equilibration during the following hour.
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34
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67349125758
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note
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3 for 24 h in borosilicate NMR tubes, while analogous runs in Teflon inserts resulted in no reaction (Table 2).
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67349281260
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2 was effected by 0.15, 0.25 and 0.15 equiv. TEMPO, respectively, as a result of its acid-mediated disporportionation that consumes stoichiometric equivalent of the acid: J.M. Bobbitt, C.L. Flores, Heterocycles 27 (1988) 509-533. Z. Ma, J.M. Bobbitt, J. Org. Chem. 56 (1991) 6110-6114. S. Kishioka, T. Ohsaka, K. Tokuda, Electrochim. Acta 48 (2003) 1589-1594. X. Wang, R. Liu, Y. Jin, X. Liang, Chem. Eur. J. 14 (2008) 2679-2685.
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2 was effected by 0.15, 0.25 and 0.15 equiv. TEMPO, respectively, as a result of its acid-mediated disporportionation that consumes stoichiometric equivalent of the acid: J.M. Bobbitt, C.L. Flores, Heterocycles 27 (1988) 509-533. Z. Ma, J.M. Bobbitt, J. Org. Chem. 56 (1991) 6110-6114. S. Kishioka, T. Ohsaka, K. Tokuda, Electrochim. Acta 48 (2003) 1589-1594. X. Wang, R. Liu, Y. Jin, X. Liang, Chem. Eur. J. 14 (2008) 2679-2685.
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FH = 441 Hz doublet in spectra of entry 19 reaction following dilution with ether and cooling below RT. D.K. Hindermann, C.D. Cornwell, J. Chem. Phys. 48 (1968) 2017-2025. C. MacLean, E.L. Mackor, J. Chem. Phys. 34 (1961) 2207-2208. G.J. Schrobilgen, J. Chem. Soc., Chem. Commun. (1988) 863-865.
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39
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67349249719
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19F NMR mass balance, of 34-79% with a median of 60%, due to precipitation/adsorption of inorganic fluoro anions as metal salts on the glass surface.
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79
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67349190884
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note
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13C HSQC spectrum.
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