Can ketone halogenation be selective?
So, I've been thinking about some theoretical and not very useful synthesis. And I started wondering, whether ketone bromination can be selective.
I wonder if I treated a ketone with one alpha position much more hindered (eg. 4-methylpenta-2-one) first with a hindered base (for example lithium
diisopropylamide) at low temperature and than withquantitative amount of bromine, would I get a ketone selectively brominated in a less hindered alpha
position? (eg. 1-bromo-4-methylpenta-2-one)
Since we are using a strong, hindered base and a limited amount of bromine, as well as kinetic controll, I guess (and only guess) it should be
possible.
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