Reduction, azobenzenes carbonyl compounds

However, efficient generation of CH2CN takes place at the second reduction potential of azobenzene using MeCN as solvent, which has been used in preparative-scale reactions initiated by cyanomethylation of benzamide [19] carbonyl compounds and a, )6-unsatured nitriles either present in situ [18,20] or added subsequently [21-23]. However, product mixtures are often complex, and although the products indicate the range of acid-base reactions possible, and the reacivity of the species generated, the electrochemical method offers little preparative advantage for these conversions. 

Whether the dianion of azobenzene is able to deprotonate MeCN (pK 31.3) has been discussed [62, 64, 68]. However, on a preparative scale generation of CH2CN takes place at the potential of the second reduction of azobenzene, and reactions initiated by cyanomethylation of benzamide [108], carbonyl compounds (or their SchifF bases) or a,)S-unsaturated nitriles either present in situ [69, 109] or added subsequently [110-112] have been studied. A mixture of products is normally obtained. 

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