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Multistep Reversible Redox Systems, XLVI 1) N,N ′‐Dicyanoquinonediimines – A New Class of Compounds, I: Synthesis and General Properties
Author(s) -
Aumüller Alexander,
Hünig Siegfried
Publication year - 1986
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198619860114
Subject(s) - chemistry , redox , titanium tetrachloride , trimethylsilyl , substituent , planarity testing , quinone , medicinal chemistry , combinatorial chemistry , titanium , stereochemistry , organic chemistry , crystallography
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.