New method for the synthesis of nitriles via the o-tert- butyldimethylsilyl aldoximes

Article abstract of DOI:10.1080/00397919808004856

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 basecatalyzed syn elimination mechanism is proposed.

Full text of DOI:10.1080/00397919808004856

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New Method for the
Synthesis of Nitriles via the
O-TERT-Butyldimethylsilyl
Aldoximes
Margarita Ortiz-Marciales a , Luis Piñero a
,
Lourdes Ufret a , Wilberto Algarín a & José
Morales a
a Department of Chemistry , University of
Puerto Rico Humacao , CUH Station, Puerto
Rico, 00791
Published online: 20 Aug 2006.
To cite this article: Margarita Ortiz-Marciales , Luis Piñero , Lourdes Ufret ,
Wilberto Algarín & José Morales (1998) New Method for the Synthesis of Nitriles
via the O-TERT-Butyldimethylsilyl Aldoximes, Synthetic Communications: An
International Journal for Rapid Communication of Synthetic Organic Chemistry,
28:15, 2807-2811, DOI: 10.1080/00397919808004856
To link to this article: http://dx.doi.org/10.1080/00397919808004856
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