In this rxn, the base KHMDS removed the benzoyl group! at -20C.
I guess the bulky silane attacked the ester and the alcohol was freed.
so the conclusion is KHMDS is quite nucleophilic.
Thursday, December 11, 2008
KHMDS is nucleophilic ??
In this rxn, the base KHMDS removed the benzoyl group! at -20C.
I guess the bulky silane attacked the ester and the alcohol was freed.
so the conclusion is KHMDS is quite nucleophilic.
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2 comments:
I don't think KHMDS should be nucleophilic. Any chance a bit of moisture got into the reaction, and this was simply hydroxide doing the hydrolysis?
yes, this sounds like a reasonable explanation.
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