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Chem Asian J. 2012 Jun;7(6):1401-7. doi: 10.1002/asia.201101046. Epub 2012 Mar 27.

Electrophilicities of bissulfonyl ethylenes.

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  • 1Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, 81377 München, Germany.


Kinetics of the reactions of bissulfonyl ethylenes with various carbanions, a sulfur ylide, and siloxyalkenes have been investigated photometrically at 20 °C. The second-order rate constants have been combined with the known nucleophile- specific parameters N and s(N) for the nucleophiles to calculate the empirical electrophilicity parameters E of bissulfonyl ethylenes according to the linear free energy relationship log k(20 °C)=s(N)(N+E). Structure-reactivity relationships are discussed, and it is shown that the electrophilicity parameters E derived in this work can be employed to define the synthetic potential of bissulfonyl ethylenes as Michael acceptors.

Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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