Effect of pressure on the Strecker synthesis of hindered α-aminonitriles from ketones and aromatic amines

The effect of high pressure is examined in Strecker reactions involving ketones, amines and trimethylsilyl cyanide. This effect is small when moderately hindered reactants are involved. However, in the case of aniline and N-methylaniline, the sensitivity of the reaction to pressure increases with increasing steric bulk of the alkyl groups of the ketone. The results confirm the merit of pressure activation as sterically demanding reactions are subject to higher pressure acceleration than their unhindered analogs. (C) 2002 Elsevier Science Ltd. All rights reserved.