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Australian Journal of Chemistry Australian Journal of Chemistry Society
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RESEARCH ARTICLE

Rearrangements in the Molecular Ions of Some ortho-Substituted Schiff Bases

T Blumenthal, M Dosen, RG Gillis and QN Porter

Australian Journal of Chemistry 46(6) 895 - 901
Published: 1993

Abstract

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.

https://doi.org/10.1071/CH9930895

© CSIRO 1993

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