Diastereoisomerism and electrochemical behaviour— an investigation of redox-active cyclophanes

(Note: The full text of this document is currently only available in the PDF Version )

Michael B. Leitner, Thomas Kreher, Helmut Sonnenschein, Burkhard Costisella and Jürgen Springer


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. H. Sonnenschein, T. Kreher, E. Gründemann, R.-P. Krüger, A. Kunath and V. Zabel, J. Org. Chem., 1996, 61, 710 CrossRef CAS.
  2. S. Hünig and F. Linhart, Liebigs Ann. Chem., 1976, 317 Search PubMed.
  3. L. Cardellini, P. Carloni, L. Greci, G. Tosi, R. Andruzzi, G. Marrosu and A. Trazza, J. Chem. Soc., Perkin Trans. 2, 1990, 2117 RSC; G. Gambini, P. Carloni, S. Zamponi, P. Conti, L. Greci and R. Marass, J. Chem. Res. (M), 1995, 135 Search PubMed.
  4. S. Hünig and H. Sonnenschein, J. Prakt. Chem., 1994, 336, 38.
  5. T. Kreher, H. Sonnenschein, L. Schmidt and S. Hünig, Liebigs Ann. Chem., 1994, 1173 Search PubMed.
  6. S. Hünig, Liebigs Ann. Chem., 1964, 676, 32 Search PubMed.
  7. D. K. Gosser, Cyclic voltammetry, VCH, New York, 1993 Search PubMed.
  8. A. J. Bard and L. R. Faulkner, Electrochemical methods, Wiley, New York, 1980 Search PubMed.
  9. D. S. Polcyn and I. Shain, Anal. Chem., 1966, 38, 370 CrossRef CAS.