Dienone–Phenol Rearrangement

Dienone–Phenol Rearrangement

Dienone–Phenol Rearrangement

In presence of acid, 4,4-disubstituted cyclohexadienone is converted into a stable 3,4-disubstituted phenol. This is known as dienone–phenol rearrangement.
Dienone–Phenol Rearrangement
Similar rearrangement is possible with a 2,2-disubstituted cyclohexadienone to 2,3-disubstituted phenol and/or a 2,6-disubstituted phenol.
Dienone–Phenol Rearrangement

Mechanism of Dienone–Phenol Rearrangement

The possible mechanism is given below-
The migratery aptitude for the two different groups present at 4,4 position can be determined by comparing the relative stability of the intermediate carbocation formed during rearrangement.
Mechanism of  Dienone–Phenol Rearrangement

Applications of Dienone–Phenol Rearrangement

Applications of  Dienone–Phenol Rearrangement

CSIR Example of  Dienone–Phenol Rearrangement

CSIR Question of  Dienone–Phenol Rearrangement