Abstract
AbstractFourier‐transform ion‐cyclotron‐resonance (FTICR) mass spectrometry has been used to uncover the mechanisms by which FeO+ dehydrates heptan‐4‐one (5a) and nonan‐5‐one (6a) in the gas phase. The study of isotopomeric ketones provides evidence that H2O loss is not due to a 1,1‐elimination, thus ruling out the intermediacy of high‐valent iron‐carbene species. Rather, H2O is generated in a formal 1,2‐elimination involving the ω/ω − 1 positions of the alkyl chain (‘remote CH bond activation’). In the consecutive alkene/H2O elimination, the olefins (ethylene from 5a and propene from 6a) originate from the terminal part of one alkyl chain, and the H‐atom is transferred to the FeO+ moiety in the course of this process, builds up together with an H‐atom from the ω/ω‐1 position of the other alkyl chain the H2O molecule. In either case, the O‐atom of H2O is provided by the FeO+ species.
Published Version
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