Multistep Reversible Redox Systems, XLVI 1)   N,N ′‐Dicyanoquinonediimines – A New Class of Compounds, I: Synthesis and General Properties | Zendy

Aumüller Alexander | Zendy; Hünig Siegfried | Zendy

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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.

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