Issue 15, 2011
From the journal:

Chemical Communications

Expanding the chemical space for push-pull chromophores by non-concerted [2+2] and [4+2] cycloadditions: access to a highly functionalised 6,6-dicyanopentafulvene with an intense, low-energy charge-transfer band†

Govindasamy Jayamurugan,a   Jean-Paul Gisselbrecht,b   Corinne Boudon,b   Franziska Schoenebeck,*a   W. Bernd Schweizer,a   Bruno Berneta  and  François Diederich*a  

* Corresponding authors

a Laboratorium für Organische Chemie, ETH Zürich, Hönggerberg, HCI, 8093 Zürich, Switzerland
E-mail: diederich@org.chem.ethz.ch
Fax: +41 44 632 1109
Tel: +41 44 632 2992

b Laboratoire d'Electrochimie et de Chimie Physique du Corps Solide, Institut de Chimie-UMR 7177, C.N.R.S., Université de Strasbourg, 4, rue Blaise Pascal, CS 90032, 67081 Strasbourg Cedex, France

Abstract

Non-concerted [2+2] and [4+2] cycloadditions between N,N-dimethylanilino-substituted 1,1,2,4,4-pentacyanobuta-1,3-diene and 4-ethynyl-N,N-dimethylaniline are controlled by solvent polarity and provide access to a highly functionalised 6,6-dicyanopentafulvene featuring an intense, low-energy charge-transfer band and to an unusual spirocyclic zwitterion, characterised by X-ray analysis.

Graphical abstract: Expanding the chemical space for push-pull chromophores by non-concerted [2+2] and [4+2] cycloadditions: access to a highly functionalised 6,6-dicyanopentafulvene with an intense, low-energy charge-transfer band

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Article information

DOI
https://doi.org/10.1039/C1CC10247H
Article type
Communication
Submitted
13 Jan 2011
Accepted
22 Feb 2011
First published
11 Mar 2011

Chem. Commun., 2011,47, 4520-4522

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Expanding the chemical space for push-pull chromophores by non-concerted [2+2] and [4+2] cycloadditions: access to a highly functionalised 6,6-dicyanopentafulvene with an intense, low-energy charge-transfer band

G. Jayamurugan, J. Gisselbrecht, C. Boudon, F. Schoenebeck, W. B. Schweizer, B. Bernet and F. Diederich, Chem. Commun., 2011, 47, 4520 DOI: 10.1039/C1CC10247H

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