Sodium Bis(trimethylsilyl)amide in the Oxidative Conversion of Aldehydes to Nitriles

The feasibility of the Me 3 Si species acting as a nucleofuge was investigated in compounds containing the NSiMe 3 moiety. Treatment of various aromatic aldehydes with 2.2 equiv. of NaN(SiMe 3 ) 2 at 185 °C in a sealed tube produced the corresponding nitriles in high yields (81–98 %). In these reactions, NaN(SiMe 3 ) 2 acted as an oxidizing agent. Results from control experiments indicate that the Me 3 Si unit can depart efficiently from the NSiMe 3 moiety of N ‐silylimine intermediates. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)