G. Knothe et al., FATTY ALCOHOLS THROUGH HYDROXYLATION OF SYMMETRICAL ALKENES WITH SELENIUM DIOXIDE TERT-BUTYLHYDROPEROXIDE, Journal of the American Oil Chemists' Society, 72(9), 1995, pp. 1021-1026
Several symmetrical alkenes were reacted with the selenium dioxide/ter
t.-butylhydroperoxide system to give three hydroxylated products each.
These products were those of allylic mono- and dihydroxylation (meso
and three dihydroxy compounds) of the double bond. Some dihydroxy prod
ucts were hydrogenated to give saturated 1,4-diols. The compounds were
characterized by nuclear magnetic resonance. The products have potent
ial for application in commercial products, such as biodiesel, lubrica
nts, greases, and cosmetics.