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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 15
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Original Articles

New Method for the Synthesis of Nitriles via the O-TERT-Butyldimethylsilyl Aldoximes

Margarita Ortiz-Marciales Department of Chemistry, University of Puerto Rico Humacao, CUH Station, Puerto Rico, 00791
,
Luis Piñero Department of Chemistry, University of Puerto Rico Humacao, CUH Station, Puerto Rico, 00791
,
Lourdes Ufret Department of Chemistry, University of Puerto Rico Humacao, CUH Station, Puerto Rico, 00791
,
Wilberto Algarín Department of Chemistry, University of Puerto Rico Humacao, CUH Station, Puerto Rico, 00791
&
José Morales Department of Chemistry, University of Puerto Rico Humacao, CUH Station, Puerto Rico, 00791
Pages 2807-2811 | Received 11 Dec 1997, Published online: 20 Aug 2006
 
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Abstract

The reaction of aromatic aldehyde oximes with TBSCl and imidazole in DMF generates the corresponding O-silylated derivative, which undergoes elimination, affording the nitrile with a high yield. For the fragmentation of the predominantly (E) isomer, a base-catalyzed syn elimination mechanism is proposed.

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