Base-promoted rearrangement of 2,3-epoxycyclohexanones to phenols

The reactions were examd. of ten 2,3-epoxycyclohexanones with NaH in (MeOCH2)2; the products were trapped by treatment with Me3CSiMe2Cl and Et3N. Generally, the main reaction products were the corresponding silylated phenols. E.g., carvone epoxide gave 66% 3,4-Me3CSiMe2O(Me)C6H3CMe:CH2. This aromatization proceeds by deprotonation at the α'-C atom followed by O-silylation, β'-proton removal, olefinic bond shift, oxirane ring cleavage, and 1,2-elimination.