Volume 2006, Issue 11 p. 2513-2516
Short Communication

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

Jih Ru Hwu

Jih Ru Hwu

Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan 30013, R.O.C., Fax: +886-3-572-1594

Search for more papers by this author
Fung Fuh Wong

Fung Fuh Wong

Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan 30013, R.O.C., Fax: +886-3-572-1594

Search for more papers by this author
First published: 11 May 2006
Citations: 21

Graphical Abstract

Abstract

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. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)