Soluble cycloannulated tetroxa[8]circulane derivatives: synthesis, optical and electrochemical properties, and generation of their robust cation–radical salts

Syntheses of soluble bicycloalkane-annulated tetraoxa[8]circulane derivatives via Lewis acid-catalyzed tetramerization of readily available cycloannulated benzoquinons is described. The ready availability of the soluble circulane derivatives allows the evaluation of their optical and electrochemical properties. These circulanes form stable (isolable) cation–radical salts upon 1-electron oxidation using antimony pentachloride and various aromatic oxidants.