Electrophilicities of trans-β-Nitrostyrenes

J.Org. Chem., 2011, 76, 9370-9378 published on 06.10.2011

The kinetics of the reactions of the trans-beta-nitrostyrenes 1a–f with the acceptor-substituted carbanions 2a–h have been determined in dimethyl sulfoxide solution at 20 Grad Celsius. The resulting second-order rate constants were employed to determine the electrophile-specific reactivity parameters E of the trans-beta-nitrostyrenes according to the correlation equation log k2(20 Grad Celsius) = sN(N + E). The E parameters range from −12 to −15 on our empirical electrophilicity scale (www.cup.lmu.de/oc/mayr/DBintro.html). The second-order rate constants for the reactions of trans-beta-nitrostyrenes with some enamines were measured and found to agree with those calculated from the electrophilicity parameters E determined in this work and the previously published N and sN parameters for enamines


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