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Journal Article

Proximity effects in the mass spectra of crowded bis(dimethylamino)arenes, I, intramolecular cyclization of ‘proton sponges’ 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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Saupe,  Thomas
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;

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https://www.sciencedirect.com/science/article/pii/S0040403900853083/pdf?md5=c7733c48572c5bbbedaff75fda714f15&pid=1-s2.0-S0040403900853083-main.pdf
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https://doi.org/10.1016/S0040-4039(00)85308-3
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Citation

Rentzea, M., Saupe, T., & Staab, H. A. (1986). Proximity effects in the mass spectra of crowded bis(dimethylamino)arenes, I, intramolecular cyclization of ‘proton sponges’ under electron impact. Tetrahedron Letters, 27(47), 5715-5718. doi:10.1016/S0040-4039(00)85308-3.


Cite as: https://hdl.handle.net/21.11116/0000-0006-939C-4
Abstract
El mass spectra of 4,5-bis(dimethylamino)phenanthrene () and the related compounds -

show base peaks corresponding to an M+·-Me2NH-H fragmentation for which the following mechanism is proposed: intramolecular hydrogen migration from one of the methyl groups to the nitrogen of the adjacent dimethylamino group, intramolecular cyclization with ejection of dimethylamine, and aromatization involving loss of H· and leading to stable N-methyl thebenidinium and phenanthridinium ions, respectively.

Crowded bis(dimethylamino)arenes show specific proximity effects in mass spectra:
by hydrogen migration, intramolecular cyclisatlon and aromatisation forms N-methyl thebenidinium ion.