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  Electrochemical oxidation and structural changes of 5,6-dihydrobenzo[c]cinnolines

Dietrich, M., Heinze, J., Krieger, C., & Neugebauer, F. A. (1996). Electrochemical oxidation and structural changes of 5,6-dihydrobenzo[c]cinnolines. Journal of the American Chemical Society, 118, 5020-5030. doi:10.1021/ja952478m.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0024-2382-5 Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0024-2383-3
Genre: Journal Article
Alternative Title : Electrochemical oxidation and structural changes of 5,6-dihydrobenzo[c]cinnolines

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JACS_118_1996_5020.pdf (Any fulltext), 305KB
 
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http://pubs.acs.org/doi/pdfplus/10.1021/ja952722%2B (Any fulltext)
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http://dx.doi.org/10.1021/ja952722+ (Any fulltext)
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 Creators:
Dietrich, Michael, Author
Heinze, Jürgen, Author
Krieger, Claus1, Author           
Neugebauer, Franz A.1, Author           
Affiliations:
1Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society, ou_1497706              

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 Abstract: The anodic oxidation of tetraphenylhydrazine (1) and various 5,6-dihydrobenzo[c]cinnoline derivatives (2-10) in liquid SO2 and CH2Cl2 was studied by cyclic voltammetry at different temperatures. All compounds could be oxidized to their respective dications and in some cases to their trications. The unusual results indicate a high internal reorganization energy during the first oxidation step. X-ray structure determinations and other findings reveal that the electron transfer reactions are accompanied by structural changes of the molecular framework. The mechanism of oxidation will be dicussed in terms of different variants. Digital simulations and experimental data give strong evidence for an EiE-DISP mechanism

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Language(s): eng - English
 Dates: 1995-08-101996-02-131996-05-29
 Publication Status: Issued
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: eDoc: 665268
DOI: 10.1021/ja952478m
URI: pubs.acs.org/cgi-bin/abstract.cgi/jacsat/1996/118/i21/abs/ja952722+.html
URI: pubs.acs.org/cgi-bin/article.cgi/jacsat/1996/118/i21/html/ja952478m.html
URI: pubs.acs.org/cgi-bin/article.cgi/jacsat/1996/118/i21/pdf/ja952722+.pdf
Other: 6810
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Title: Journal of the American Chemical Society
  Other : J. Am. Chem. Soc.
  Abbreviation : JACS
Source Genre: Journal
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Publ. Info: American Chemical Society
Pages: - Volume / Issue: 118 Sequence Number: - Start / End Page: 5020 - 5030 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870