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- W1999702950 abstract "The electrochemical reductions of 9-methoxyfluorene (FlHOCH3), 9-methylfluorenol (Fl(CH3)OH) and 9-fluorenol (FlHOH) have been studied at a platinum electrode in DMF−0.1 M (n-Bu)4NClO4 over the temperature range −51°⩽T⩽22°C. The anion radicals of these compounds undergo heterolytic cleavage of the carbon—oxygen bond to give a fluorenyl radical (FlR, where R=H or CH3) and OR−. The subsequent redox behavior and follow-up solution reactions differ for each compound and depend upon the availability of a C9 and/or a hydroxylic proton. In the case of Fl(CH3)OH, the electrogenerated OH− abstracts a hydroxylic proton from unreacted starting material to give Fl(CH3)O−. Although this species is not oxidized, it is reduced at more negative potential to an unstable dianion radical that rapidly and indiscriminately abstracts proton. When a hydroxylic proton is not available, as in the case of FlHOCH3, the electrogenerated CH 3O− abstracts a proton from a component of the solvent-electrolyte system rather than from the C9 position. FlOCH3− is then formed slowly, but this is the result of C9 proton transfer from FlHOCH3 to the electrogenerated FlH−. Here, FlOCH3−, like FlH−, is oxidized irreversibly to its radical, but is not reduced in this solvent-electrolyte system. The OH− produced in the decomposition of FlHOH− abstracts only the hydroxylic proton from unreacted FlHOH. The cathodic wave for the reduction of FlHO− and the anodic wave for the oxidation of FlR− are kinetically controlled and result from the relatively slow abstraction of the thermodynamically more acidic C9 proton from FlHOH by FlHO− and FlH respectively." @default.
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- W1999702950 date "1982-02-01" @default.
- W1999702950 modified "2023-09-25" @default.
- W1999702950 title "The effect of kenetic vs. thermodynamic acidity on the redox behavior of several 9-hydroxy- and 9-methoxyfluorenes" @default.
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- W1999702950 doi "https://doi.org/10.1016/0022-0728(82)87005-8" @default.
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