Selective thermolysis of the enol forms of acetoacetates during gas chromatography, revealed by combined matrix-isolation Fourier transform infrared and mass spectrometry

The thermal decompositions of methyl and ethyl acetoacetates have been observed by combined gas chromatography (GC)-mass spectrometry-matrix-isolation Fourier transform infrared spectrometry. Under the conditions employed, keto and enol forms could be separated by GC and, by careful control of inter...

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Bibliographic Details
Published in:Journal of Chromatography A 1994-11, Vol.685 (2), p.287-293
Main Authors: Jackson, P., Carter, D., Dent, G., Cook, B.W., Chalmers, J.M., Dunkin, I.R.
Format: Article
Language:English
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Summary:The thermal decompositions of methyl and ethyl acetoacetates have been observed by combined gas chromatography (GC)-mass spectrometry-matrix-isolation Fourier transform infrared spectrometry. Under the conditions employed, keto and enol forms could be separated by GC and, by careful control of interface temperatures, the thermolysis of the individual components could be studied. Each enol acetoacetate form was almost completely converted to a keto-ketene and an alcohol. The keto-acetoacetate forms were only partially decomposed, with reaction products identical to those of the enol forms, indicating that the preferred mechanism of thermal degradation is via the enol-acetoacetate form.
ISSN:0021-9673
DOI:10.1016/0021-9673(94)00672-5