Issue 10, 1997
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Structural and electrochemical properties of a novel N,N′-dialkyl-substituted quinone diimine

Oliver Temme,   Sabine Laschat,   Roland Fröhlich,   Birgit Wibbeling,   Jürgen Heinze  and  Petra Hauser  

Abstract

trans,trans-3,3,7,7,10,10,14,14-Octamethyl-1,2,3,4,4a,7,7a,8,9,10,11,11a,14,14a-tetradecahydroquino[2,3-b]acridine 5, formed by a Lewis acid-catalyzed biscyclization of N-arylbisimine 3 and subsequent autoxidation, represents the first stable example of the unexplored class of N,N′-dialkyl-substituted quinone diimines. The X-ray crystal structure of 5 exhibits the following features: space group P21/c; a ribbon-like arrangement of two parallel strands along the b-axis. The smallest intermolecular distance between two quinoid systems is 4.846 Å and therefore any close aromatic contacts in this material can be precluded. A chemically reversible single electron reduction at E0 = –1.87 V has been observed by cyclic voltammetry.

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Article information

DOI
https://doi.org/10.1039/A700691H
Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1997, 2083-2085

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Structural and electrochemical properties of a novel N,N′-dialkyl-substituted quinone diimine

O. Temme, S. Laschat, R. Fröhlich, B. Wibbeling, J. Heinze and P. Hauser, J. Chem. Soc., Perkin Trans. 2, 1997, 2083 DOI: 10.1039/A700691H

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