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#1 2010-08-18 17:53:50

orgopete
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Sigmatropic rearrangement of allyl phenyl ether to allyl phenol

This is electrocyclic reaction is a Claisen rearrangement. The scheme shown below shows the bonds that are made and broken in the rearrangement step. Because that intermediate is the less stable form of a ketone (cyclohexadienone) than phenol, a tautomerization reaction is required to complete the reaction. Because the reaction medium will contain phenol, an intermolecular proton transfer is a likely mechanism. For the sake of convenience, I illustrated this reaction by using neutral water as a base followed by protonation of the anion with the hydronium ion.

     http://www.curvedarrow.com/chem/ZZ087B3936.jpg
     This example is excerpted from A Handbook of Organic Chemistry Mechanisms, available at http://www.curvedarrowpress.com/ or Amazon.com

A better analysis of these reactions is described by orbital symmetry rules. See the answer and links to a question about molecular orbitals here:
http://orgo.curvedarrow.com/punbb/viewt … pid=97#p97

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