Multiple aromatische sigmatropische Umlagerung von γ, γ‐Dimethylallyl‐phenyläther

The rearrangement of γ,γ‐dimethylallyl phenyl ether (1), contrary to previous reports, gives a mixture of 4‐(γ,γ‐dimethylallyl)‐phenol (2), 2‐(α,β‐dimethylallyl)‐phenol (3) and 2,2,3‐trimethylcoumaran (4). The ratio of the reaction products is dependent on the solvent and the reaction temperature. The mechanism for the reaction is discussed in terms of multiple sigmatropic rearrangements.