Multistep Reversible Redox Systems, XLVI¹⁾<i>N,N</i>′‐Dicyanoquinonediimines – A New Class of Compounds, I: Synthesis and General Properties

Abstract

Abstract A new class of quinone derivatives, the dicyanodiimines 2 , 21 , and 23 , has been synthesized by the reaction of the corresponding quinones with bis(trimethylsilyl)carbondiimide ( 8 ) and titanium tetrachloride. A wide variety of substrates, even those which contain bulky groups and those which exhibit a strong influence on the redox potential, has been prepared. A route starting from p ‐phenylenediamines 4 via the N,N ′‐dicyanodiamines 6 has been found to be much more limited. The spectroscopic properties of compounds 2 , 21 , and 23 are discussed with respect to their syn / anti isomerizations as well as substituent effects on their planarity.