Issue 0, 1984
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

The configurational stability of vinyl carbanions derived from monosubstituted activated ethylenes

Ben-Ami Feit,   Uri Melamed,   Heike Speer  and  Richard R. Schmidt  

Abstract

The configurational stability of vinyl carbanions derived from the 1 -substituted activated ethylenes, acrylonitrile and methyl acrylate, was investigated. The pure cis-isomers of the corresponding β-deuterio-olefins were treated with benzophenone in the presence of a base in several solvents (diethyl ether, tetrahydrofuran, and diethyl ether-hexane). cis–trans Mixtures of the corresponding α-[hydroxy-[(diphenyl)methyl] derivatives formed were isolated and their composition determined. The mechanism of the formation of the two isomeric products is discussed. The vinyl carbanion derived from the β-deuterioacrylonitrile was configurationally stable, while that derived from the corresponding acrylic ester was configurationally unstable.

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Article information

DOI
https://doi.org/10.1039/P19840000775
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1984, 775-780

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The configurational stability of vinyl carbanions derived from monosubstituted activated ethylenes

B. Feit, U. Melamed, H. Speer and R. R. Schmidt, J. Chem. Soc., Perkin Trans. 1, 1984, 775 DOI: 10.1039/P19840000775

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