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Supramolecular Chemistry Volume 19, 2007 - Issue 6
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Original Articles

First Synthesis of Upper Rim Mono and Dinitrone Calix[4]arene Derivatives

Sofiane Ben Sdira Equipe Chimie Supramoléculaire Appliquée, CNRS UMR 5634, Université Claude Bernard Lyon 1, 43 bd du 11 Novembre 1918, F-69622, Villeurbanne cedex, France
,
Roselyne Baudry Equipe Chimie Supramoléculaire Appliquée, CNRS UMR 5634, Université Claude Bernard Lyon 1, 43 bd du 11 Novembre 1918, F-69622, Villeurbanne cedex, France
,
Caroline P. Felix Equipe Chimie Supramoléculaire Appliquée, CNRS UMR 5634, Université Claude Bernard Lyon 1, 43 bd du 11 Novembre 1918, F-69622, Villeurbanne cedex, FranceCorrespondence[email protected]
,
Marie-Béatrice A. Giudicelli Equipe Chimie Supramoléculaire Appliquée, CNRS UMR 5634, Université Claude Bernard Lyon 1, 43 bd du 11 Novembre 1918, F-69622, Villeurbanne cedex, France
,
Francis Vocanson Equipe Chimie Supramoléculaire Appliquée, CNRS UMR 5634, Université Claude Bernard Lyon 1, 43 bd du 11 Novembre 1918, F-69622, Villeurbanne cedex, France
,
Monique Perrin Equipe Chimie Supramoléculaire Appliquée, CNRS UMR 5634, Université Claude Bernard Lyon 1, 43 bd du 11 Novembre 1918, F-69622, Villeurbanne cedex, France
&
Roger J. Lamartine Equipe Chimie Supramoléculaire Appliquée, CNRS UMR 5634, Université Claude Bernard Lyon 1, 43 bd du 11 Novembre 1918, F-69622, Villeurbanne cedex, France
 show all
Pages 393-398 | Received 11 Jul 2006, Accepted 08 Sep 2006, Published online: 19 Sep 2007
 
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Abstract

A new class of calix[4]arene derivatives bearing one or two nitrone groups on the upper rim has been synthesized using the oxidation of chiral imines with hydrogen peroxide. The imine intermediates were obtained via amination of the diformyl derivative. The 1H NMR spectra and X-ray data indicated a 1,3-disubstituted cone conformation for the imine derivatives and the existence of a single (E,E) isomer. The structural identity of the nitrone derivatives was confirmed from NMR, IR and ES-MS data. Both mono and dinitrone calix[4]arenes were in E configuration.

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