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Methylation of 1,3-cyclopentanedione, 1,3-cyclohexanedione, and 1,3-cycloheptanedione with iodomethane in aprotic solvents in the absence and in the presence of 18-crown-6

J. Šraga and P. Hrnčiar

Department of Organic Chemistry, Faculty of Natural Sciences, Komenský University, 816 31 Bratislava

 

Abstract:  Anions of 1,3-cyclopentanedione, 1,3-cyclohexanedione, and 1,3-cyclohep­tanedione were methylated with iodomethane in aprotic solvents. It was found that the highest amount of О-derivative was formed in nonpolar solvents (diethyl ether, tetrahydrofuran). The presence of 18-crown-6 did not affect the C/O ratio of methylation of the investigated 1,3-cycloalkanedione anions significantly. The reasons for different solvent effects on the C/O ratio of alkylation of cyclic and acyclic 1,3-dicarbonyl compounds are discussed.

Full paper in Portable Document Format: 351a119.pdf

 

Chemical Papers 35 (1) 119–126 (1981)

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