MULTISTEP REDOX SYSTEMS .61. SYNTHESIS OF 1,4-BIS(2-METHYL-INDOLIZIN-1-YL-METHYL)-BENZENE AND RELATED MODEL COMPOUNDS

The synthesis of 1a, in which two 1-indolizine units are connected by a p-xylylene bridge is preformed from its 3,3'bis-acetyl derivative 1b via the precursors 8-11. This route was first tested by the synthesis of benzyl indolizines 2b and 2a via the pyridyl-aminopropanol 3a. 2a can be oxidatively dimerized to the 3,3'-bis-indolizine 6 which forms a perfectly reversible two step redox system with K-SEM=4.7 x 10(5).