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Updated: Jan 8, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Reactivity of a Sodium Anion with Alkenes: 1-Electron vs 2-Electron Reductions
Huanxin Zhang1, Nathan Davison1, Jack M Hemingway2
1School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, U.K.
Abstract:
The sodium anion (sodide) is an uncommon alkali metal species, whose reactivity has been scarcely studied, with previous reports limited to decomposition and quenching reactions of ill-characterized species formed in situ. Based on our recent report of the first gram-scale synthesis of a well-characterized sodide complex, [Na+(2,2,2-cryptand)]Na- (1), we now describe its reactivity with phenyl-substituted ethylenes and a cyclic polyolefin. Depending on the substitution pattern, 1 mediates either 1-electron or 2-electron reduction. Reaction with a cyclic multiolefin, 1,3,5,7-cyclooctatetraene (COT), exhibits two-electron reduction to produce COT2- species.
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