Pages

▼

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.
at

2 comments:

  1. AnonymousDecember 11, 2008 at 4:39 PM

    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?

    ReplyDelete
  2. Weiwei TIANDecember 11, 2008 at 5:37 PM

    yes, this sounds like a reasonable explanation.

    ReplyDelete

Your comments are welcome.