Abstract
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, 2006.