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Synthesis 2008(11): 1805-1807  
DOI: 10.1055/s-2008-1032117
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© Georg Thieme Verlag Stuttgart · New York

A One-Step, Safe Synthesis of 2,4-Dinitrostyrene and Related (Di)nitrodivinylbenzenes via Stille Coupling

Nathalie Eloy, Eric Pasquinet*, Eric Grech, Frank David-Quillot, Olivier Besnard, Didier Poullain
CEA Le Ripault, BP16, 37260 Monts, France
Fax: +33(2)47345142; e-Mail: eric.pasquinet@cea.fr;
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Publication History

Received 12 December 2007
Publication Date:
06 March 2008 (online)

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Abstract

A one-step synthesis of 2,4-dinitrostyrene is described. Based on a Stille coupling, the procedure is more amenable to scale-up than the existing methods that require longer reaction sequences and hazardous nitration processes. This easily polymerizable monomer was isolated using a continuous extraction method. The reaction was extended to the synthesis of two other related vinyl monomers including the previously unknown 1,3-dinitro-4,6-divinylbenzene.

Key words

Stille reaction - cross-coupling - polymers - nitro compounds - styrenes

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