Zinc-Promoted Reactions. 9. The Fate of the Cyano Group in the Reduction of Simple Cyanoketones and N-Cyanoamines

Article abstract of DOI:10.1016/S0040-4020(01)85302-3

The Zn/AcOH reduction of 1 leads only to the carbonyl reduction, while C-decyanation occurs in the case of 2.The mechanism of the latter reaction is discussed.The N-decyanation of N-cyanoamines 3 and 4 involves an ionic mechanism, leading to N-acyl derivatives and isocyanic acid, the latter compound being ultimately reduced to formic acid.