1953
DOI: 10.1021/j150510a026
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Polarographic Studies in Formamide Solutions

Abstract: Stilbene, anthracene, and 9-anisylidenefiuorene are reduced stepwise polarographi-cally in anhydrous acetonitrile and in dimethylformamide. Triphenylethylene, tetra-phenylethylene, styrene, and 1,1-diphenylethylene give only one reduction wave. Large-scale electrolytic reductions in these solvents indicate that carbanion inter-mediates exist for a short period of time. 1,2,3,4-Tetraphenylbutane and meso-diphenyl succinic acid have been prepared electrolytically from stilbene in dimethylformamide.

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Cited by 14 publications
(7 citation statements)
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“…Like for furan, photoinduced electron transfer (PET) with formation of solvent-separated ion pairs (SSIP) is energetically unfeasible in unpolar solvents such as benzene or cyclohexane. The oxidation potential for 4 is too high to enable exergonic electron transfer (Δ G SSIP [benzene, ε: 2.3] = +0.62 eV) from the triplet state of benzaldehyde . This lack in driving force can be compensated by increasing the solvent polarity, which reduces the coulomb term in the Rehm−Weller equation .…”
Section: Resultsmentioning
confidence: 99%
“…Like for furan, photoinduced electron transfer (PET) with formation of solvent-separated ion pairs (SSIP) is energetically unfeasible in unpolar solvents such as benzene or cyclohexane. The oxidation potential for 4 is too high to enable exergonic electron transfer (Δ G SSIP [benzene, ε: 2.3] = +0.62 eV) from the triplet state of benzaldehyde . This lack in driving force can be compensated by increasing the solvent polarity, which reduces the coulomb term in the Rehm−Weller equation .…”
Section: Resultsmentioning
confidence: 99%
“…The reduction of the IR amino features is accompanied by the appearance of new bands ascribed to the presence of secondary amides. [14][15][16] In particular, for the reaction with acetic anhydride, the new n(C]O) band is seen at 1706 cm À1 (see Fig. 3, part (c) for compd 2) with an accompanying n(N-H) single band at 3344 cm À1 (Fig.…”
mentioning
confidence: 96%
“…[9] The dielectric constant for benzene was assumed to be 2.27. [10] The E Ox for 1a was determined through cyclic voltammetry in acetonitrile relative to Ag/AgCl and was 0.93 Ϯ 0.05 V. The same determination for 1f gave 0.88 Ϯ 0.05 V and 1.07 Ϯ 0.05 V for 1b. With these results, we could calculate the ∆G values reported in Table 2.…”
Section: Resultsmentioning
confidence: 99%