Formation of 1,1-dimethylallyl derivatives by reaction of 3,3-dimethylallyl halides with copper(II) chelates of acetylacetone and methyl acetoacetate

Abstract

Alkylation of the copper(II) chelates of acetylacetone and methyl acetoacetate by 3,3-dimethylallyl halides yields both 3,3-dimethylallyl and 1,1-dimethylallyl products. Formation of 1,1-dimethylallyl derivatives of these β-polyketide analogues appears to be the results of a direct C-alkylation, and is a significant characteristic of the copper chelate reactions, which has not been observed previously with other alkylation reactions of β-diketones or β-keto-esters.