Dilithiation of α,β-disubstituted Activated Olefins: α,β-dilithiocinnamonitrile

Ben Ami Feit*, Brigitte Haag, Richard R. Schmidt

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations


cis- and trans-cinnamonitrile were treated with an excess of LDA in an aprotic medium to give a high yield of one preferred isomer of PhC(Li)=C(CN)Li (C.N.-2Li). The chemistry and stereochemistry of its reactions with various electrophiles (MeOD, Mel, IBuI, RCHO, MeSSMe) was studied and discussed. a-Substituted and α,β-disubstituted derivatives of cis- and trans-cinnamonitrile were obtained. The reaction with MeOD resulted exclusively in a quantitative yield of trans-PhCD=CDCN. It is suggested that substitution at Catakes place first to yield an equilibrium mixture of the corresponding 0-lithiated intermediates: m-PhC(Li)=C(E)CN and trans-PhC(Li)=C(CN)E. The type and structure of the products obtained in the reaction of this equilibrium mixture with electrophiles depends on factors affecting the nucleophilic reactivity and configurational stability of the Cβ—Li bond of each of these two β-lithiated cinnamonitrile derivatives.

Original languageEnglish
Pages (from-to)3825-3831
Number of pages7
JournalJournal of Organic Chemistry
Issue number17
StatePublished - 1 Aug 1987


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