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Electron impact and chemical ionization mass spectra of bis(methoxycarbonyl) [2.2](2,5)pyridinophanes. Formation of quinolizinium ions under electron impact

MPS-Authors
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Rentzea,  Marina
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Hasselbach,  Hans-Joachim
Max Planck Institute for Medical Research, Max Planck Society;

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Staab,  Heinz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

External Resource

https://onlinelibrary.wiley.com/doi/epdf/10.1002/oms.1210210612
(Any fulltext)

https://doi.org/10.1002/oms.1210210612
(Any fulltext)

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Citation

Rentzea, M., Hasselbach, H.-J., & Staab, H. A. (1986). Electron impact and chemical ionization mass spectra of bis(methoxycarbonyl) [2.2](2,5)pyridinophanes. Formation of quinolizinium ions under electron impact. Organic Mass Spectrometry, 21(6), 367-370. doi:10.1002/oms.1210210612.


Cite as: https://hdl.handle.net/21.11116/0000-0006-93E1-5
Abstract
For four isomeric bis(methoxycarbonyl)[2.2](2,5)pyridinophanes differing only in the mutual orientation of the two nicotinic ester units, electron impact mass spectra were measured. The fragmentations observed distinguish surprisingly well between the isomers, depending on the transannular substitution pattern. Of special interest is that for one isomer the otherwise unimportant ion at m /z 298 is found as base peak. This ion is formed by expulsion of HCN from the molecular ion, transannular cycloaddition and aromatization to a stable quinolizinium ion. Fragmentation pathways of the isomers are compared, and chemical ionization and negative ion chemical ionization mass spectra are discussed.