89114-46-5Relevant academic research and scientific papers
Reactions of Oxime Dianions with Electrophiles: An Attempt to Use Aldoximes as Acyl Anion Equivalents and the Synthesis of 2,5-Disubstituted Furans
Ager, David J.
, p. 2748 - 2759 (2007/10/02)
The oxime of benzaldehyde (3), when treated with n-butyl-lithium, gave a mixture of the vinyl-lithium (5) and benzonitrile (4).Despite its potential as an acyl anion equivalent, the dianion (5) could only be formed in moderate yield and was always accompanied by elimination products.Aliphatic aldoximes (1) gave the alkyl anion with n-butyl-lithium, but were only alkylated in the case of the Z-isomer.The oxime of furfuraldehyde (8) underwent deprotonation at the 5-position of the furan ring with n-butyllithium - N,N,N',N' - tetramethylethylenediamine in tetrahydrofuran.The resultant dianion (10) was reacted with a variety of electrophiles to give the 2,5-disubstituted furan (9).
THE SYNTHESIS OF 2,5-DISUBSTITUTED FURANS
Ager, David J.
, p. 5441 - 5444 (2007/10/02)
The dianion derived from the oxime of furfuraldehyde (1) reacts with electrophiles at the 5-position of the furan ring; subsequent hydrolysis of the oxime provides a useful method for the synthesis of 2,5-disubstituted furans.
