Rearrangement and Loss of Bromine Radical and CO from Some Bromobenzyl Alcohols following Electron Ionisation

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...

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Published in:European journal of mass spectrometry (Chichester, England) England), 2000-04, Vol.6 (2), p.135-141
Main Authors: Kubišta, Jiří, Hanuš, Vladimír, Havlíček, Libor, Hanuš, Jan, Halada, Petr, Kuzma, Marek
Format: Article
Language:English
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Summary: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.
ISSN:1469-0667
1751-6838
DOI:10.1255/ejms.333