Issue 46, 2007
From the journal:

Chemical Communications

New strong organic acceptors by cycloaddition of TCNE and TCNQ to donor-substituted cyanoalkynes†

Philippe Reutenauer,a   Milan Kivala,a   Peter D. Jarowski,a   Corinne Boudon,b   Jean-Paul Gisselbrecht,b   Maurice Grossb  and  François Diederich*a  

* Corresponding authors

a Laboratorium für Organische Chemie, ETH Zürich, Hönggerberg, HCI, Switzerland
E-mail: diederich@org.chem.ethz.ch
Fax: +41 44 632 1109

b Laboratoire d'Electrochimie et de Chimie Physique du Corps Solide, Institut de Chimie-LC3-UMR 7177, CNRS, Université Louis Pasteur, 4, rue Blaise Pascal, France

Abstract

Donor-substituted 1,1,2,4,4-pentacyanobuta-1,3-dienes and a cyclohexa-2,5-diene-1,4-diylidene-expanded derivative were prepared by a [2 + 2] cycloaddition of tetracyanoethene (TCNE) or 7,7,8,8-tetracyanoquinodimethane (TCNQ) to anilino-substituted cyanoalkynes, followed by retro-electrocyclisation; they feature intense bathochromically-shifted intramolecular charge-transfer bands and undergo their first one-electron reductions at potentials similar to those reported for TCNE and TCNQ.

Graphical abstract: New strong organic acceptors by cycloaddition of TCNE and TCNQ to donor-substituted cyanoalkynes

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Article information

DOI
https://doi.org/10.1039/B714731G
Article type
Communication
Submitted
25 Sep 2007
Accepted
22 Oct 2007
First published
31 Oct 2007

Chem. Commun., 2007, 4898-4900

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New strong organic acceptors by cycloaddition of TCNE and TCNQ to donor-substituted cyanoalkynes

P. Reutenauer, M. Kivala, P. D. Jarowski, C. Boudon, J. Gisselbrecht, M. Gross and F. Diederich, Chem. Commun., 2007, 4898 DOI: 10.1039/B714731G

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