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0023282886
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K. Kaikiuchi M. Ue M. Takeda T. Tadaki Y. Kato T. Nagashima Y. Tobe H. Koike N. Ida Y. Odaira Chem. Pharm. Bull. 1987 35 617
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(1987)
Chem. Pharm. Bull.
, vol.35
, pp. 617
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Kaikiuchi, K.1
Ue, M.2
Takeda, M.3
Tadaki, T.4
Kato, Y.5
Nagashima, T.6
Tobe, Y.7
Koike, H.8
Ida, N.9
Odaira, Y.10
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17
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57549103930
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DigitalSimulations were performed by using DigiElch Pro software
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DigitalSimulations were performed by using DigiElch Pro software
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18
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57549113091
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The decomposition of the aromatic radical-anion is faster when the aromatic nucleus bears an inductive electron substituent, such as a methyl group. The methoxy-substituted benzoates are slightly more difficult to reduce but the rate of decomposition of the corresponding anion-radical is similar to that derived from the toluate. Finally, in the case of the simple benzoate, competing addition of the in situ generated radical to the para position of the aromatic ring has been observed
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The decomposition of the aromatic radical-anion is faster when the aromatic nucleus bears an inductive electron substituent, such as a methyl group. The methoxy-substituted benzoates are slightly more difficult to reduce but the rate of decomposition of the corresponding anion-radical is similar to that derived from the toluate. Finally, in the case of the simple benzoate, competing addition of the in situ generated radical to the para position of the aromatic ring has been observed
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19
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57549118493
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We suspect the tetrabutylammonium cation to be the hydrogen atom donor since only degradation occurred when lithium perchlorate was used as the supporting electrolyte
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We suspect the tetrabutylammonium cation to be the hydrogen atom donor since only degradation occurred when lithium perchlorate was used as the supporting electrolyte
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20
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57549088818
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4 and with 100 ml of NMP, freshly distilled under argon, 600 mg (0.6 mmol) of 9-fluorenyl toluate, dissolved in a little NMP, were added to the cathodic compartment and the solution was stirred and heated up to 130°C. Then, the intensity of the current was fixed at 90 mA and the mixture was electrolysed until completion of the reaction, as shown by TLC or by GC. The cell was then cooled down to room temperature and the catholyte was carefully diluted with 100 ml of 4 N HCl. The resulting solution was extracted 4 times with 30 ml of ether
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f = 0.7), affording the title compound as a white powder in 50% yield. This material proved to be identical to an authentic sample of fluorene
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21
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57549111226
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A plausible explanation could be a reaction between the fluorenyl radical and the oxide layer of the electrode. Indeed, copper and lead electrodes are usually covered by a reactive oxide layer. In this regard, we have obtained a similar result when using Cgraphite electrodes in non-degassed NMP.
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A plausible explanation could be a reaction between the fluorenyl radical and the oxide layer of the electrode. Indeed, copper and lead electrodes are usually covered by a reactive oxide layer. In this regard, we have obtained a similar result when using Cgraphite electrodes in non-degassed NMP.
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22
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57549105638
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No Kolbe-like dimers have been detected in this reaction. This could originate from the rapid capture of the radical by the large excess of tetra-alkylammonium salts or, as in the case of the benzylic substrates, by the fast reduction of this radical into the corresponding anion. (See Table 5, entry 4)
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No Kolbe-like dimers have been detected in this reaction. This could originate from the rapid capture of the radical by the large excess of tetra-alkylammonium salts or, as in the case of the benzylic substrates, by the fast reduction of this radical into the corresponding anion. (See Table 5, entry 4).
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