Dicyanobenzenes electroreduction

However, the study of the entropy of formation of anion radicals formed by electroreduction of selected organic species such that the charge is localized at an unshielded heteroatom (e.g., / -dicyanobenzene [97]) shows that this parameter is linearly dependent on the acceptor number of solvents. 

The reactivity of cyanide ion with aryl radicals generated electrochemically in liquid ammonia from 2-, 3- and 4-chlorobenzonitriles was reported by Amatore and coworkers. The coupling between the aryl radicals and the nucleophile appears to be the key step of a Srn reaction. In these reactions the C—Cl bond was cleaved in the radical anion formed by electroreduction of the chlorobenzonitrile, giving a radical that then reacted with cyanide to yield dicyanobenzenes. The steps involved in the reaction sequence are described in Yoshida s review. ... 

Dicyanobenzene was converted into 3-cyanobenzoic acid by using the bacterium Rhodococcus rhodochrocus ". Intramolecular electron transfer involving isomeric forms of dicyanobenzene was investigated in detaiP and the mechanisms of electroreduction of all three isomers were studied. When dicyanobenzene was used as catalyst in photoamination reactions of arenes, the first step of the reaction was the formation of an aryl radical cation by electron transfer from the aromatic hydrocarbon to m-dicyano-benzene. ... 

Electroreductions of organic catalysts 9-phenylanthracene (9-PA) and l,2-dicyanobenzene > (1,2-DCB or o-phthalonitrile) were chemically reversible and diffusion controlled at cyclic voltammetric (CV) scan rates between about 0.2 and 50 V/s in aqueous 0.1 M CTAB containing 0.1 M tetra-ethylammonium bromide (TEAB). The anion radicals of 9-PA and 1,2-DCB were stabilized against reaction with proton donors by the cationic micellar... 

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