Synthesis and Electrochemical Properties of Benzonaphthodioxin-6,11-quinones and Their N,N'-Dicyano Quinone Diimine Derivatives

Article abstract of DOI:10.1021/jo00004a042

The reaction of 2,3-dichloro-1,4-naphthoquinone (1) and catechols 2 in pyridine affords a series of substituted benzonaphtho<2,3-e><1,4>dioxin-6,11-quinones 3.The latter compounds are transformed to the corrsponding N,N'-dicyano quinone diimines 4, by treating them with N,N'-bis(trimethylsilyl)carbodiimide.The electrochemical studies of compounds of the type 3 and 4 in DMF and CH2Cl2, respectively, by means of cyclic voltammetry are reported.The experimental reduction potentials provide information on electron-electron repulsion in the dianionic states of 3 and 4,and hence on their potential use as acceptor components in charge-transfer complexes and organic conductors.