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Preparation and some properties of 1,3-cyclotridecanedione and 1,3-cyclotetradecanedione

J. Donovalová, J. Šraga, and P. Hrnčiar

Department of Organic Chemistry, Faculty of Natural Sciences, Komenský University, CS-842 15 Bratislava

Abstract: 1,3-Cyclotridecanedione (IIIа) and 1,3-cyclotetradecanedione (Illb) have been prepared by a three-step synthesis from diethyl dodecanedioate and tridecanedioate respectively, and the structure of by-products of first two reactions has been proved. By means of 'H-n.m.r. and infrared spectroscopy it has been found out that IIIа and lllb exist in the ketoenol form which is stabilized by intramolecular hydrogen bond. Methylation of the anions of IIIа and lllb took place at the carbon atoms in low yields. Reaction of IIIа with diazomethane did not afford the expected product of O-methylation but 2,2'-methylenedi-1,3-cyclotridecanedione (VII) was isolated.

Full paper in Portable Document Format: 376a809.pdf

Chemical Papers 37 (6) 809–817 (1983)