TY - JOUR
T1 - The configurational stability of vinyl carbanions derived from monosubstituted activated ethylenes
AU - Feit, Ben Ami
AU - Melamed, Uri
AU - Speer, Heike
AU - Schmidt, Richard R.
PY - 1984
Y1 - 1984
N2 - 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-irans 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.
AB - 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-irans 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.
UR - http://www.scopus.com/inward/record.url?scp=37049108989&partnerID=8YFLogxK
U2 - 10.1039/p19840000775
DO - 10.1039/p19840000775
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AN - SCOPUS:37049108989
SN - 1472-7781
SP - 775
EP - 780
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
ER -