Lithium diisopropylamide undergoes an addition reaction to the methyleneamino moiety of the title Schiff's bases substituted with a cyano group at the ortho or para position of the aniline, but mediates tautomerization of the unsubstituted and meta-substituted derivatives into secondary enamines. Only the tautomerization is observed for lithium 2,2,6,6-tetramethylpiperidide-mediated reactions.
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ACKNOWLEDGMENTS are made to the PetroleumR esearchF und, administeredb y the American Chemical Society, and NIH (Grants # AI27196 and S07-RR07171) for support of this research. The Varian VXR-400 NMR spectrometerw as obtained with partial support from an award by the NSF Chemical InstrumentationP rogram (CHEM-8409599).