
%0 Journal Article
%A Blumenthal, T 
%A Dosen, M 
%A Gillis, RG 
%A Porter, QN 
%T Rearrangements in the Molecular Ions of Some <I>ortho</I>-Substituted Schiff Bases
%J Australian Journal of Chemistry
%D 1993/06/01
%V 46
%N 6
%P 895-901
%K 
%R https://doi.org/10.1071/CH9930895
%U https://www.publish.csiro.au/paper/CH9930895 
%X Under electron ionization conditions, the ortho-substituted Schiff bases N-benzylidene-o-toluidine (1a), N-(o-methylbenzylidene)aniline (1b), N-salicylideneaniline (1c) and N-(o-methoxybenzylidene)aniline (1d) give fragment ions which have been shown by collision-activated mass-analysed ion kinetic energy spectra to have the structure of the protonated molecular ions of indole (2), benzofuran (3), and 1,2-benzisoxazole (4). The molecular ion of N-(o-methylbenzylidene)-o-toluidine (1f) gives as fragment ions not only the protonated molecular ion (2) of indole and the tropylium ion but also the molecular ion of anthracene. Attempts to find supporting evidence for a mechanism for this rearrangement by deuterium labelling of a methyl group in (1b), such as (1g), have been unsuccessful. 
