50515-43-0Relevant articles and documents
The Allopolarization Principle and its Applications, VI. The Alkylation of Enolate Anions: Polarity and Regioselectivity
Gompper, Rudolf,Vogt, Hans-Hubert,Wagner, Hans-Ulrich
, p. 1644 - 1652 (2007/10/02)
The O/C methylation ratio in the reaction of sodium enolates with dimethylsulfate depends on the polar (electronic) effect of substituents.The relative ?-charge density Px/y = lx/ly can be used as a measure for the polarity of ambifunctional anions; in case of enolate anions PO/C = lO/lC.The change of the regioselectivity Sf = log QO/QC in the alkylation of enolates is a function of a change in the polarity PO/C; ΔSf=f(ΔPx/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: Alkylation, Enolate Anions