Electrophilicities of Bissulfonyl Ethylenes

Chem. Asian Journal, 2012, 7, 1401-1407 published on 27.03.2012
Chem. Asian J.
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)=sN(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.
TU München