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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: faust on May 18, 2006, 02:13:01 PM

Title: 1,4 degradation of aryl ester?
Post by: faust on May 18, 2006, 02:13:01 PM

Hello.

I'm working on this kind of reaction (see the attachment)

But the article say that when the acetic anhydride is replaced by phenyl acid anhydride, there is "a high tendendy of 1,4 elimination or aromatic ester residues within the cyclohexane scaffold. Nevertheless, the use of phenyl acetic chloride could be a good replacement"

I don't really see what is this 1,4 degradation of aromatic ester. Could you show me the mecanism?

And why I don't have such degradation with phenyl acetic chloride?

Thank you