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Eur. J. Mass Spectrom. 6, 135 - 141 (2000)

Rearrangement and loss of bromine radical and CO from some bromobenzyl alcohols following electron ionisation

Jiri Kubista and Vladimir Hanus*
J. Heyrovsky Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, Dolejskova 3, 182 23 Prague 8, Czech Republic
Libor Havlicek
First Faculty of Medicine, Charles University Prague, Na bojisti 3, 121 08 Prague, Czech Republic
Jan Hanus
Isotope Laboratory, Institute of Experimental Botany, Academy of Sciences of the Czech Republic, Videnska 1083, 142 20 Prague 4, Czech Republic
Petr Halada
Institute of Microbiology, Academy of Sciences of the Czech Republic, Videnska 1083, 142 20 Prague 4, Czech Republic
Marek Kuzma
Institute of Chemical Technology, Technicka 5, 166 28 Prague 6, Czech Republic

ABSTRACT:
The electron ionisation spectra of bromine-containing derivatives of benzyl alcohol are often dominated by ions which do not contain bromine. We use the experimental data on a series of selected bromobenzyl alcohols to elucidate the easy loss of bromine atoms. In this process, arene-bonded bromines are displaced by hydrogens which originate from the benzyl group. Thus, we conclude that this reaction occurs during the "hydrogen ring-walk". The suggested reaction mechanism and structures of intermediates, which can be considered, are discussed and graphically illustrated.

Keywords: electron ionisation, fragmentation, benzyl alcohol, hydrogen ring-walk, rearrangement, ring expansion and ring contraction

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