Reactions

Mechanistically, the bond between C1 of the allyl group and the oxygen breaks and the two 𝜋-bonds (C2=C3 and C4=C5) both shift inward by one position, giving the new 𝜋-bonds at C1=C2 and C5=O in the product. In the case of an aryl allyl ether, the ring is re-aromatized via tautomerization after the rearrangement, yielding the corresponding phenol. It is important to note that the transition state (TS) is preferentially chair-like, in which the substituents prefer equatorial positions, that gives predictable relative stereochemistry at the newly formed C–C bond.
The formation of the C=O bond, which is thermodynamically more stable than the C=C bond of a vinyl ether, makes this reaction irreversible in most practical cases.