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From: Michael B. Smith (smith$##$nucleus.chem.uconn.edu)
Date: Fri Oct 22 1999 - 15:49:51 EDT


Re:
barnabas liau wrote:
> I have a weird idea. wittig reaction can be easily performed on ketone or
> aldehyde. can anyone please tell me if is possible for a cyclic ester?! if
> not, is it because the reaction simply can't happen or fear of hydrolysis
> (saponification) that may take place?





As mentioned in a previous response, the Tebbe reagent performs this
transformation. The Petasis reagent (Cp2TiMe2 - see JACS, 1990, 112, 6392)
is easier to prepare and handle and does the same thing. Classical Wittig
reactions do not work, but these Ti-based reagent work very well.

Professor Michael B. Smith
Department of Chemistry
University of Connecticut
55 N. Eagleville Road, U-60
Storrs, Connecticut USA 06269-3060

phone: 860-486-2881
fax: 860-486-2981
email: smith$##$nucleus.chem.uconn.edu
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