Separation of keto-enol tautomers in beta-ketoesters: a gas chromatography-mass spectrometric study

The gas chromatographic behaviour for some beta -ketoesters was studied. Ad ditionally, the feasibility of the gas chromatographic separation of the co rresponding tautomer forms was examined. In this work mass spectrometric de tection allowed identification of both keto and enol forms and an estimatio n of their relative amounts for methylacetoacetate, alpha -chloromethylacet oacetate, ethylacetoacetate and alpha -chloroethylacetoacetate. This findin g demonstrates slow tautomerisation kinetics permit ting the chemical ident ity maintenance of the tautomers. (C) 2001 Elsevier Science B.V. All rights reserved.