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Electrophilicities of bissulfonyl ethylenes
Asahara, Haruyasu,Mayr, Herbert
supporting information; experimental part, p. 1401 - 1407 (2012/07/28)
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 sN 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
