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.
H. B. Henbest, W. R. Jackson and B. C. G. Robb, J. Chem. Soc. B, 1966, 803 DOI: 10.1039/J29660000803
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