Collect. Czech. Chem. Commun. 1990, 55, 695-703

On the origin of base concentration effect on stereo- and regioselectivity in alkoxide-promoted E2 reactions: A consequence of substrate solvation by metal ions

Jiří Závada, Magdalena Pánková and Antonín Vítek

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


The title problem has been investigated in the reaction of 2-decyl bromide with t-C4H9OK/t-C4H9OH system employing 18-crown-6 ether and an "inert" salt (t-C4H9OLi) as mechanistic probes. From olefin-distribution data and a subsidiary kinetic evidence it has been inferred that the investigated effect originates from a concentration-dependent substrate solvation by metal ions in the transition state.