256453-25-5Relevant academic research and scientific papers
α,β-Unsaturated nitriles: Preparative MgO elimination
Fleming,Shook
, p. 8847 - 8851 (2000)
Double deprotonation of β-hydroxynitriles with MeMgCl (2.1 equiv.) generates a dianion that ejects MgO to provide the corresponding α,β-unsaturated nitriles. Structurally diverse β-hydroxynitriles readily eliminate MgO providing an expedient route to highly substituted α,β-unsaturated nitriles. (C) 2000 Published by Elsevier Science Ltd.
Unsaturated nitriles: Stereoselective MgO eliminations
Fleming, Fraser F.,Shook, Brian C.
, p. 3668 - 3672 (2007/10/03)
α,β-Unsaturated nitriles are readily synthesized by eliminating MgO from β-hydroxynitriles. Deprotonating acyclic, and cyclic, β-hydroxynitriles with excess MeMgCl smoothly generates dianion intermediates that eject MgO with concurrent formation of α,β-unsaturated nitriles. Alternatively, sequential addition of lithioacetonitrile and MgBr2 to aldehydes and ketones generates magnesium alkoxides in situ that eliminate MgO upon addition of MeMgCl. The MeMgCl-induced MgO eliminations smoothly generate α,β-unsaturated nitriles from hindered ketones that are otherwise difficult to synthesize.
