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Sodium Bis(trimethylsilyl)amide in the Oxidative Conversion of Aldehydes to Nitriles
Author(s) -
Ru Hwu Jih,
Fuh Wong Fung
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600134
Subject(s) - chemistry , moiety , oxidizing agent , trimethylsilyl , amide , medicinal chemistry , organic chemistry
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)