Polarographic Studies in Acetonitrile and Dimethylformamide

Abstract

Stilbene, anthracene, and 9-anisylidenefiuorene are reduced stepwise polarographically in anhydrous acetonitrile and in dimethylformamide. Triphenylethylene, tetraphenylethylene, styrene, and 1,1-diphenylethylene give only one reduction wave.Large-scale electrolytic reductions in these solvents indicate that carbanion intermediates 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.

Stanley Wawzonek and the Introduction of Polar Aprotic Solvents into Organic Electrochemistry

“…It is hard to underestimate the influence of this first study 14 and the simultaneous work of Hoijtink 18 of solvent effects on subsequent research in organic electrochemistry, not simply the electrochemistry of unsaturated hydrocarbons. Previously, a solvent would have been chosen simply on the basis of convenience, such as the solubility of the substrate to be studied in it and perhaps also ease of purification.…”

“…It describes the polarographic and preparative scale reductions of stilbene, anthracene, 9-anisylidenefluorene, triphenylethylene, tetraphenylethlene, styrene, and 1,1-diphenylethylene in acetonitrile (AN) and/or dimethylformamide (DMF). 14 The key discovery described in the manuscript was the fact that several of the compounds (stilbene among them) exhibit two one-electron waves in AN or DMF instead of the two-electron waves previously observed for them in aqueous dioxane. 7 The positioning of the waves was intriguing: the two-electron wave in aqueous media 7 is at the same potential as the first wave in DMF or AN.…”

“…13 That paper described relatively uninteresting electrochemical measurements, by contemporary standards, on the polarographic reduction of simple inorganic ions in acetonitrile. However, the second paper in the series, titled "Polarographic Studies in Acetonitrile and Dimethylformamide," 14 had an immediate effect on the development of organic electrochemistry and is the topic of this article. It describes the polarographic and preparative scale reductions of stilbene, anthracene, 9-anisylidenefluorene, triphenylethylene, tetraphenylethlene, styrene, and 1,1-diphenylethylene in acetonitrile (AN) and/or dimethylformamide (DMF).…”

Electrochemical Reaction of Organic Compounds in Ionic Liquids

“…15.26), which undergoes rapid protonation to form 1,2-diphenylethane (Eq. 15.27) [22][23][24][25][26][27]. The reductive coupling of 2-cyclohexen-1-one (xxvi) has been investigated extensively in aqueous, organic, and a mixture of these solvents, because this reaction is able to afford different products, such as 3-(3-oxocyclohexyl)cyclohexan-1-one (xxvii), 3-(1-hydroxycyclohex-2-enyl)cyclohexanone (xxviii), and 1-(1-hydroxycyclohex-2-enyl)cyclohex-2-enol (xxix), depending on the reaction conditions (Scheme 15.3) [7,28,29].…”

Chronopotentiometric Studies on the Decomposition Products of N, N-Dimethylformamide at Platinum and Gold Electrodes

“…•¬ (5) To know the mechanisms of the decomposition reactions, however, more detailed experiments must be performed.…”