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Proximity effects in the mass spectra of crowded bis(dimethylamino)arenes: Part II—Rearrangements of the molecular radical cations of ‘proton sponges’ by reciprocal methyl/hydrogen transfer

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
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Brox,  Wolfgang
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://analyticalsciencejournals.onlinelibrary.wiley.com/doi/10.1002/oms.1210240602
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https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/epdf/10.1002/oms.1210240602
(Any fulltext)

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Citation

Rentzea, M., Saupe, T., Brox, W., & Staab, H. A. (1989). Proximity effects in the mass spectra of crowded bis(dimethylamino)arenes: Part II—Rearrangements of the molecular radical cations of ‘proton sponges’ by reciprocal methyl/hydrogen transfer. Organic Mass Spectrometry, 24(6), 367-372. doi:10.1002/oms.1210240602.


Cite as: https://hdl.handle.net/21.11116/0000-000A-EE9D-A
Abstract
The EI induced fragmentation pathways of 4,5-bis(dimethylamino)fluorene, 4-(d6-dimethylamino)-5-(dimethylamino)fluorene, 4,5-bis(d6-dimethylamino)fluorene, 4-(dimethylamino)-5-methylaminofluorene, 4,5-bis-(methylamino)fluorene, 4-amino-5-methylaminofluorene, 1,8-bis(dimethylamino)naphthalene, 1,8-bis(d6-dimethyl-amino)-naphthalene and 1,8-bis(dimethylamino)-2,7-dimethoxynaphthalene were investigated. A mechanism is pro-posed for the surprising elimination of CH3NH2 from the molecular ion, followed by loss of C2H5·, C2H4 and CH3CN and for the accompanying cyclizations to stable heterocyclic ions: prior to fragmentation the molecular radical ion rearranges to new, distonic radical ions by reciprocal H and CH3 transfers between the adjacent dimethylamino groups. Each of these new, isomeric molecular ions decomposes subsequently in a characteristic way.