Diastereoisomerism and electrochemical behaviour— an investigation of redox-active cyclophanes
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The influence of diastereoisomerism on the electrochemical
behaviour of the atropisomeric cyclophanes 1a and 1b was found by
cyclovoltammetric studies. Compound 1a can be oxidized and reduced
reversibly in a two step redox process similar to that of model compound
2. In contrast, 1b shows a different electrochemistry. As a result of a
detailed investigation of 1b a complex reaction scheme can be postulated
starting with a chemical reaction after the first oxidation step. The
special spatial situation in 1b makes possible this EC mechanism
reaction, which does not occur in 1a or in unbridged
biindolizines.
[1] R. Krüger,et al. Novel Redox-Active Cyclophanes Based on 3,3'-Biindolizines: Synthesis and Chirality. , 1996, The Journal of organic chemistry.
[2] D. S. Polcyn,et al. Multistep Charge Transfers in Stationary Electrode Polarography. , 1966 .