Comparison of the Ozonolysis Products of the Methylnaphthalenes and Dimethylnapthalenes in Hexane, Methanol, and Water

摘要

The ozonolyses of 1- and 2-methylnaphthalene and 1,2-, 1,3-, 1,4-, and 2,3-dimethylnaphthalene were performed in dilute aqueous solution, and the products which resulted were compared to products from similar reactions performed in n-hexane and methanol. Gas chromatography, gas chromatography-mass spectrometry, and gas chromatography-Fourier transform infrared spectrometry were used. All products characterized in the three solvents resulted from the normal ozonolysis of either one or two double bonds in the naphthalene ring system. Products resulting from the ozonolysis of two double bonds were typical. Products which resulted from the ozonolysis of only one double bond were not expected. Reactions in water yielded large amounts of these mono-ozonolysis products compared with the reactions in n-hexane and methanol. A second major difference in the aqueous ozonolyses was that these reactions yielded aldehydes and ketones exclusively as products. The reactions in the organic solvents contrasted sharply with the reactions in water by yielding large amounts of carboxylic acids as well as aldehydes and ketones. (ERA citation 09:033822)