The feasibility of the Me3Si species acting as a nucleofuge was investigated in compounds containing the NSiMe3 moiety. Treatment of various aromatic aldehydes with 2.2 equiv. of NaN(SiMe3)2 at 185 °C in a sealed tube produced the corresponding nitriles in high yields (81-98 %). In these reactions, NaN(SiMe3)2 acted as an oxidizing agent. Results from control experiments indicate that the Me3Si unit can depart efficiently from the NSiMe3 moiety of N-silylimine intermediates.
關聯:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2006(11)2513 ~2516
