Effect of pressure on stetter reactions: synthesis of hindered aliphatic acyloins and γ-ketonitriles

Abstract

The pressure effect is examined in thiazolium salt catalyzed addition reactions of aldehydes (Stetter reaction and acyloin condensation). Both reactions are not affected by pressure when they involve unhindered substrates. Their response to pressure, however, is strongly enhanced with increasing bulkiness of the reactants. The result is in line with the general pressure effect on sterically congested reactions.

Keywords:

• Stetter reaction
• Acyloin synthesis
• High pressure activation
• Steric hindrance