Electrophilic and radical reactivity of ionized aminohydroxycarbene toward alkenes

Abstract : Ion molecule reactions between ionized aminohydroxycarbene, [NH2COH](.+),1, and several representative alkenes (ethene, propene, 1-butene, 2-butene) were studied by Fourier transform ion cyclotron resonance mass spectrometry. Condensation processes were evidenced by the fragmentation pattern of the elusive collision complex which exhibits the characteristic behavior of the corresponding ionized aliphatic amide. Mechanistic pathways, corroborated by collision induced dissociation and deuterium labeling experiments and by G2 molecular orbital calculations, are proposed to explain the observed pattern. Proton and hydrogen atom transfer were also detected in several cases.
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Submitted on : Friday, December 13, 2013 - 5:25:54 PM
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Guy Bouchoux, Julia Chamot-Rooke. Electrophilic and radical reactivity of ionized aminohydroxycarbene toward alkenes. International Journal of Mass Spectrometry, Elsevier, 2002, 219 (3), pp.625-641. ⟨10.1016/S1387-3806(02)00708-X⟩. ⟨hal-00918092⟩

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