The alkylation of 2-methylcyclopentane-1,3-dione (A) with 2-(1-naphthyl)ethyl bromide gives only the O-alkylation product. Mixtures of C- and O-alkyl derivatives are obtained with (A) when phenacyl or 1-naphthacyl bromide is employed. The C- to O-alkyl ratio is lower with (A) than with the homologous diketone 2-methyl-cyclohexane-1,3-dione; a possible explanation for this difference is advanced.
D. Rosenthal and K. H. Davis, J. Chem. Soc. C, 1966, 1973 DOI: 10.1039/J39660001973
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