Characterization of artefacts produced by treatment of organic acids with diazomethane

Add time:07/27/2019    Source:sciencedirect.com

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 CC 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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