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

Miller, J.A. and Black, Rona and Larkin, J. and Nonhebel, D.C. and Wood, H.C.S., Scrimego.C.M (1973) Formation of 1,1-dimethylallyl derivatives by reaction of 3,3-dimethylallyl halides with copper(ii) chelates of acetylacetone and methyl acetoacetate. Journal of the Chemical Society, Perkin Transactions 1 (6). pp. 603-606. ISSN 1472-7781

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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 -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 -diketones or -keto-esters.