Direct conversion of bromohydrins to ketones by a free radical elimination of hydrogen bromide.
Secondary beta-bromo alcohols can be transformed directly to ketones in very good yields by a free radical process. Tertiary beta-bromo alcohols do not react while the primary ones are transformed to aldehydes in lower yields. The reaction involves an abstraction of a hydrogen atom alpha to an OH group, followed by elimination of the bromine atom and subsequent tautomerization of an enol to a ketone.
Dolenc
Darko
D
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, SI-1000 Ljubljana, Slovenia. darko.dolenc@uni-lj.si
Harej
Maja
M