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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

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.

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Item Permalink: https://hdl.handle.net/21.11116/0000-000A-EE9D-A Version Permalink: https://hdl.handle.net/21.11116/0000-000A-EE9E-9
Genre: Journal Article
Alternative Title : 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

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OrganicMassSpectrometry24_1989_367.pdf (Any fulltext), 383KB
 
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Rentzea, Marina1, Author           
Saupe, Thomas1, Author           
Brox, Wolfgang2, Author           
Staab, Heinz A.1, Author           
Affiliations:
1Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society, ou_1497706              
2Max Planck Institute for Medical Research, Max Planck Society, ou_1125545              

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 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.

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Language(s): eng - English
 Dates: 1988-08-091989-10-171989-06
 Publication Status: Issued
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/oms.1210240602
 Degree: -

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Title: Organic Mass Spectrometry
  Abbreviation : Org. Mass Spectrom.
Source Genre: Journal
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Publ. Info: Chichester [u.a.] : Wiley
Pages: - Volume / Issue: 24 (6) Sequence Number: - Start / End Page: 367 - 372 Identifier: ISSN: 2376-3884
CoNE: https://pure.mpg.de/cone/journals/resource/2376-3884