Abstract
When α,β-unsaturated acids and α-keto acids react with diazomethane not only are the corresponding methylates produced, but also diazomethane is added to the CC double bond or to the oxo group. The gas chromatographic and mass spectral behaviour of these undesired products and some further artefacts produced in the hot inlet lines of a gas chromatograph are described. The mass spectra and retention indices allowed the structural assignment of several “unknown” compounds found previously in the methylated acid fraction of urine. A detailed analysis of the reaction of α-oxo acids with diazomethane revealed that, besides the already known oxirane methyl esters, homologous esters are also produced by an insertion reaction.
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