Das Allopolarisierungsprinzip und seine Anwendungen, VI [1] Die Alkylierung von Enolatanionen: Polarität und Regioselektivität / The Allopolarization Principle and its Applications, VI [1] The Alkylation of Enolate Anions: Polarity and Regioselectivity
Open Access
- 1 December 1981
- journal article
- Published by Walter de Gruyter GmbH in Zeitschrift für Naturforschung B
- Vol. 36 (12) , 1644-1652
- https://doi.org/10.1515/znb-1981-1227
Abstract
The O/C methylation ratio in the reaction of sodium enolates with dimethylsulfate depends on the polar(electronic) effect of substituents. The relative π-charge density Px/y = 1x/1y can be used as a measure for the polarity of ambifunctional anions; in case of enolate anions Po/c = 1o/1c-The change of the regioselectivity Sf = log Qo/Qc in the alkylation of enolates is a function of the change in the polarity Po/c; ⊿Sf = f (⊿Px/y). The polar effect of substituents influences the charge control during the alkylation process via a change of the polarity of the enolate system: The higher the polarity of the anion, the stronger the charge control and the higher the yield of enol ether (O-alkylation).Keywords
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