| Abstract
| - α,β-Unsaturated nitriles are readily synthesized by eliminating MgO from β-hydroxynitriles.Deprotonating acyclic, and cyclic, β-hydroxynitriles with excess MeMgCl smoothly generates dianionintermediates that eject MgO with concurrent formation of α,β-unsaturated nitriles. Alternatively,sequential addition of lithioacetonitrile and MgBr2 to aldehydes and ketones generates magnesiumalkoxides in situ that eliminate MgO upon addition of MeMgCl. The MeMgCl-induced MgOeliminations smoothly generate α,β-unsaturated nitriles from hindered ketones that are otherwisedifficult to synthesize.
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