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🆕 Date Issued:
1983
🗄 Date Available:2019-01-02
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Zur intermediären Existenz von Ethylenfluoronium-Ionen in der Gasphase

Ciommer, Bernhard; Schwarz, Helmut

FG Organische Chemie

The long-sought ethylen fluoronium ion (2) is generated as an intermediate in the dissociative ionization of 1-fluoro-2-(p-methyl)phenoxy ethane (4). However, prior to collisionally induced dissociation 2 undergoes ring-opening, associated with hydrogen migration, to form 1-fluoroethyl cation (3). Other decomposition pathways of the molecular ions of 4 involve (i) direct formation of 3 via a combination of C-O-cleavage (loss of ArO -) and [1,2] hydrogen migration (18%) and (ii) complete positional loss of the a-and β-methylene hydrogen atoms (34%). The remaining 48% of the molecular ions of 4 dissociate via anchimeric assistance of the fluorine in the elimination of ArO·, thus giving rise to the formation of 2.
fluoronium ionsneighbouring group participationgaseous ionscollisional activationmass spectrometry
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