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

Stilbene, anthracene, and 9-anisylidenefluorene 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.