Determination of the Electrophilicity Parameters of Diethyl Benzylidenemalonates in Dimethyl Sulfoxide: Reference Electrophiles for Characterizing Strong …

O Kaumanns, R Lucius, H Mayr

Index: Kaumanns, Oliver; Lucius, Roland; Mayr, Herbert Chemistry - A European Journal, 2008 , vol. 14, # 31 p. 9675 - 9682

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Citation Number: 50

Abstract

Abstract The second-order rate constants of the reactions of nine substituted diethyl benzylidenemalonates 1 a–i with the carbanions 2 a–e have been determined spectrophotometrically in dimethyl sulfoxide (DMSO). Product studies show that the nucleophiles attack regioselectively at the electrophilic C [DOUBLE BOND] C double bond of the Michael acceptors to form the carbanionic adducts 4. The correlation log k (20 C)= s ...