Neighboring??Group Participation in the Gas Phase. Loss of benzaldehyde from [(benzyloxy) methyl] dialkylsilyl??substituted 1, 3??dithianes

J Fässler, P Huber, S Bratovanov, L Bigler…

Index: Faessler, Juerg; Huber, Priska; Bratovanov, Svetoslav; Bigler, Laurent; Bild, Norbert; Bienz, Stefan Helvetica Chimica Acta, 1995 , vol. 78, p. 1855 - 1862

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Abstract

Abstract [(Benzyloxy) methyl] dialkylsilyl-substituted 1, 3-dithianes show in CI-MS an abundant loss of benzaldehyde from the [M+ H]+ quasi-molecular ion. The fragmentation is explained with an intramolecular redox process, where a hydride is proposed to be transferred from the benzyl position to a neighboring thionium ion. This would form a particle that could readily lose benzaldehyde as a neutral fragment. The CI-MS results provide an ...