The above reaction just won't go on my hand despite excess base.
But, the following rxn is so quick that the rxn is done within 10 min at rt.
Monday, December 8, 2008
An interesting reaction
The above reaction just won't go on my hand despite excess base.
But, the following rxn is so quick that the rxn is done within 10 min at rt.
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8 comments:
Think you might have been deprotonating the alcohol?
So what? a protonated alcohol will stop the reaction?
Dunno. Did nothing happen at all, or did you get crazy side products?
(I'm a mediocre organiker at best, which is why I stick to materials ;) )
i wonder what would happen if you were to attempt the reaction on the alcohol but with a longer chain between the -OH and the -Br, and 2+ equivalents of NaH.
To: Ψ*Ψ
No rxn at all.
st recovered after 24 hr.
to: stokes_brolandish
this kind of rxn actually presented in some literature, they just use a unprotected alcohol and they got a decent yield.
I'd bet you're deprotonating the alcohol and making the epoxide there. Even though the ring is strained, the intramolecular effect makes this a pretty fast, and probably competitive reaction.
While the epoxide might still be a decent electrophile, there's no base left to deprotonate the amide to make it nucleophilic. Also, depending on the conditions it might be escaping as a gas.
In my opinion, the best suggestion to get around it is exactly what you did - use a protected alcohol.
To Russ
you may be right.
thank you for your comment.
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