Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane?
New Journal of Chemistry Pub Date: 2016-03-07 DOI: 10.1039/C5NJ03672K
Abstract
Cyclic 1,4-dicarbonyl compounds can be easily obtained by mixing a solution of aryl methyl or alkyl methyl ketone enolate anions with 1,3-diiodo-2,2-dimethylpropane in DMSO. This represents the first example of dimerization of ketone enolate anions using a simple diiodoalkane as a reagent followed by subsequent double alkylation with bis-iodide yielding a cyclopentane adduct. This methodology allows the use of a simple potassium tert-butoxide as a base at room temperature for the formation of three C–C bonds resulting in a relatively complex five-membered ring diketone structure under transition-metal-free conditions.
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Journal Name：New Journal of Chemistry
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CAS no.: 89640-58-4
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