Electronic effects in the reactions of olefins with permanganate ion and with osmium tetroxide

Abstract

The oxidation of olefins (alicyclic compounds and stilbenes) by permanganate ion is accelerated by electron-attracting substituents, but these groups retard the reactions of the olefins with osmium tetroxide. For the stibene oxidations, approximate ρ values obtained were: 0·65 for the permanganate reactions in aqueous dioxan and –0·55 for the osmium tetroxide reactions in dioxan.