
TY  - JOUR
A1  - Blumenthal, T 
A1  - Dosen, M 
A1  - Gillis, RG 
A1  - Porter, QN 
T1  - Rearrangements in the Molecular Ions of Some <I>ortho</I>-Substituted Schiff Bases
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1993
VL  - 46
IS  - 6
SP  - 895
EP  - 901
KW  - 
UR  - https://doi.org/10.1071/CH9930895 
N2  - 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. 
ER  -

