Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 11, Issue 2, Pages 619-627Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200400715
Keywords
electrospray ionization; enolates; iron; keto esters; mass spectrometry; Michael addition
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Solutions of Fe-III salts and beta-keto esters have been investigated by means of electrospray ionization mass spectrometry. The complexes formed in such solutions have been considered previously as active intermediates in Fe-III-catalyzed Michael additions. By using different Fe-III salts with a set of beta-keto esters, cation and anion mass spectra were analyzed and the effects of ester concentration, the role of the counterion, and the structure of the ester employed are discussed. Depending on the basicity of the ester, an increase of its concentration may lead to a decrease in the concentration of iron complexes observed in the mass spectra. Counterions with strong binding affinities to iron are found to capture the metal as ferrates, thereby removing the metal from the catalytic cycle.
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