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

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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.

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