Selective reduction of α,β-unsaturated nitriles with combined reducing agent bismuth chloride/sodium borohydride was written by Ren, Ping-Da;Shao, Dong;Dong, Ting-Wei. And the article was included in Youji Huaxue in 1997.Quality Control of 2-Cyclohexylacetonitrile This article mentions the following:
Bismuth chloride/sodium borohydride reacts chemoselectively with α,β-unsaturated nitriles in 95% ethanol to give the corresponding saturated nitriles with good yields. E.g., reduction of PhCH:CHCN with NaHBH4/BiCl3 in 95% EtOH at room temperature for 3 h gave 90% PhCH2CH2CN. The reduction mechanism was discussed. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Quality Control of 2-Cyclohexylacetonitrile).
2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Quality Control of 2-Cyclohexylacetonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts