European journal of organic chemistry

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

J Ru Hwu, F Fuh Wong

Index: Jih, Ru Hwu; Fung, Fuh Wong European Journal of Organic Chemistry, 2006 , # 11 p. 2513 - 2516

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Citation Number: 11

Abstract

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 ...