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Journal Article

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

MPS-Authors
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Krieger,  Claus
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

/persons/resource/persons94523

Neugebauer,  Franz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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http://pubs.acs.org/doi/pdfplus/10.1021/ja952722%2B
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http://dx.doi.org/10.1021/ja952722+
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Citation

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.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-2382-5
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