324538-20-7

Upstream product

• 18492-37-0 (+/-)-fenchone 
• 7787-20-4 (1R)-fenchone 
• 75-05-8 acetonitrile 
• 366013-96-9 2-((1R,2R,4S)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)acetonitrile 
• 439689-16-4 ((1S,2S,4R)-2-Hydroxy-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-acetonitrile 
• 324538-17-2 (1R,4S)-2-(2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]hept-2-yl)acetonitrile 

Relevant academic research and scientific papers

Unsaturated nitriles: Stereoselective MgO eliminations

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.

α,β-Unsaturated nitriles: Preparative MgO elimination

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.