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When Both Ortho Positions on the Aromatic Ring Are Blocked

Question 42

Essay

When both ortho positions on the aromatic ring are blocked, the enolization of the Claisen
rearrangement product is impossible.In this case two sequential [3,3]-shifts occur, affording a
trisubstituted phenol.Starting from the following allyl aryl ether, draw the arrow formalism for
both [3,3] shifts, showing the intermediates and the final product. When both ortho positions on the aromatic ring are blocked, the enolization of the Claisen rearrangement product is impossible.In this case two sequential [3,3]-shifts occur, affording a trisubstituted phenol.Starting from the following allyl aryl ether, draw the arrow formalism for both [3,3] shifts, showing the intermediates and the final product.

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