Addition and lithiation reactions of N-(1-phenylalkylidene)anilines with lithium dialkylamides

Lucjan Strekowski, Steven Patterson, Marek T. Cegla, Roman L. Wydra, Agnieszka Czarny, Donald B. Harden

Research output: Contribution to journalArticlepeer-review

4 Scopus citations


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.

Original languageEnglish (US)
Pages (from-to)5197-5200
Number of pages4
JournalTetrahedron Letters
Issue number39
StatePublished - 1989

Bibliographical note

Funding Information:
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).


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