Diastereoisomerism and electrochemical behaviour - An investigation of redox-active cyclophanes

The influence of diastereoisomerism on the electrochemical behaviour of the atropisomeric cyclophanes la and Ib was found by cyclovoltammetric studies, Compound la can be oxidized and reduced reversibly in a two step redox process similar to that of model compound 2, In contrast, Ib shows a different electrochemistry, As a result of a detailed investigation of Ib a complex reaction scheme can be postulated starting with a chemical reaction after the first oxidation step, The special spatial situation in Ib makes possible this EC mechanism reaction, which does not occur in la or in unbridged biindolizines.