From: Jon Kremsky (jkremsky$##$primeorg.com)
Date: Thu Sep 25 2003 - 08:35:26 EDT
The problem is not the oxidant, but the relative stabilities of the two
tautomers. Presumably you are always getting the same ratio of enol to
ketone. There is a solvent effect in the equilibrium. Try a non-polar,
aprotic solvent such as carbon tetrachloride or hexane: that ought to favor
the ketone form. Take a look at House's book for a full discussion.
Jon Kremsky
-----Original Message-----
From: everybody-admin$##$orglist.net [mailto:everybody-admin$##$orglist.net]On
Behalf Of Chun Li
Sent: Wednesday, September 24, 2003 6:34 PM
To: everybody$##$orglist.net
Subject: ORGLIST:DMP oxidation
Hi there,
I have difficulties when I tried to oxidize a phenethyl alcohol to ketone
using Dess-Martin Periodinane. I always got enol and ketone mixture, and it
seems that enol form is much more stable (because of the elongated
conjugation) and easier to be crystalized than ketone form. Is there any
body has the same problem when using DMP? Anyone know how I can avoid enol
formation? Thanks a lot!
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