Heterocycles. XX. : Reactions of 2"-Methoxymethoxychalcone Epoxides under Acidic Conditions

The effect of substitutents on the formation of products in the reactions of 2"-methoxymethoxychalcone epoxides under acidic conditions has been examined. Regardless of the 6"-substitutent, the presence of a 4'-hydroxyl group results in the exclusive formation of flavanonols. The presence of a 4'-methoxyl group directs the reactions toward the competitive formation of flavanonols and glycol monomethyl ethers or toward the exclusive formation of glycol monomethyl ethers, depending on the bulk of the 6"-substituent.