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  Proximity effects in the mass spectra of crowded bis(dimethylamino)arenes, I, intramolecular cyclization of ‘proton sponges’ under electron impact

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.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0006-939C-4 Version Permalink: https://hdl.handle.net/21.11116/0000-0006-939D-3
Genre: Journal Article

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TetrahedronLett_27_1986_5715.pdf (Any fulltext), 198KB
 
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 Creators:
Rentzea, Marina1, Author           
Saupe, Thomas2, Author           
Staab, Heinz A.1, Author           
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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: 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.

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Language(s): eng - English
 Dates: 1986-09-051986
 Publication Status: Issued
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1016/S0040-4039(00)85308-3
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Title: Tetrahedron Letters
  Other : Tetrahedron Lett.
Source Genre: Journal
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Publ. Info: Oxford : Pergamon
Pages: - Volume / Issue: 27 (47) Sequence Number: - Start / End Page: 5715 - 5718 Identifier: ISSN: 0040-4039
CoNE: https://pure.mpg.de/cone/journals/resource/954925448772