Cathodic Synthesis of Dicyanodiphenyl Diselenide From Phenylselenobenzonitrile

Article abstract of DOI:10.1016/S0040-4020(01)89796-9

The catodic reduction of 2-, 3- and 4-(phenylseleno)benzonitrile has been carried out in N,N-dimethylformamide and acetonitrile, at mercury, Pt, and glassy carbon electrodes.The first reduction step is accompanied by C-Se bond breaking.In the presence of an acid (fluorene, phenol, Bu4NSO4H), cyanobenzeneselenolate anions are thus generated in high yields, together with a small amount of benzeneselenolate anions (about 85percent and 15percent yiels, respectively).The former anions can be oxidised either anodically or chemically by air in alkaline aqueous solutions, and so 2,2'-, 3,3'- and 4,4'-dicyanodiphenyldiselenide are isolated in 59percent, 70percent and 75percent yields, respectively.