The Claisen rearrangement involves heating allyl phenyl ether to roughly , yielding -allylphenol. Wh — Aromatic Hydrocarbons Chemistry Question
Question
The Claisen rearrangement involves heating allyl phenyl ether to roughly $200^\circ C$, yielding $o$ -allylphenol. Which of the following best describes the mechanism of this specific transformation?
💡 Solution & Explanation
The Claisen rearrangement of allyl phenyl ethers is a purely thermal reaction and requires no catalyst. It is an intramolecular, concerted [1]-sigmatropic rearrangement. The allyl group migrates to the ortho position via a highly ordered, six-membered cyclic transition state, initially forming a non-aromatic dienone which rapidly tautomerizes to the highly stable $o$ -allylphenol to restore aromaticity.