Synthesis 2010(5): 844-848  
DOI: 10.1055/s-0029-1218590
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

First TDAE-Mediated Double Addition of Nitrobenzylic Anions to Aromatic Dialdehydes

Thierry Juspin, Gamal Giuglio-Tonolo, Thierry Terme, Patrice Vanelle*
Laboratoire de Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, Universités d’Aix-Marseille I, II et III - CNRS, UMR 6264, Laboratoire Chimie Provence, 27 Boulevard J. Moulin, 13385 Marseille Cedex 05, France
Fax: +33(4)91794677; e-Mail: patrice.vanelle@pharmacie.univ-mrs.fr;
Further Information

Publication History

Received 19 October 2009
Publication Date:
07 December 2009 (online)

Abstract

We report herein the first tetrakis(dimethylamino)ethylene (TDAE)-mediated double addition of nitrobenzylic anions to aromatic dialdehydes such as terephthalaldehyde and isophthalaldehyde, and have developed a new methodology that allows us to observe the double addition. This TDAE-mediated approach is an original and mild method with which to generate tri-aromatic diols.