A study of several different reductions of α, β-unsaturated nitriles by NaBH4 shows that these proceed by way of a 1:4 addition to form saturated nitriles. At long reaction times, hydrolysis products or those of substitution of the saturated nitrile are observed. The relative rates of reduction follow the order: 2-phenyl-2-butenenitrile 1 > 2,3-diphenyl-2-propenenitrile 2 > 3-phenyl-2-propenenitrile 3 > 2-butenenitriIe 4. [Journal translation]
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