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Paper | Regular issue | Vol 57, No. 12, 2002, pp.2239-2254
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9571
Synthesis and Characterisation of Extended π-Bonding Systems in Cycloimmonium Ylides Derived from the 4,4’-Bipyridine

Ludovic Depature* and Gheorghe Surpateanu

*Laboratoire de Synthèse Organique et Environnement, Maison de la Recherche Environnement Industriel de Dunkerque, Université du Littoral, 145 rue Maurice Schumann, 59140 Dunkerque, France

Abstract

Disubstituted cycloimmonium ylides derived from the 4,4’-bipyridine with one, two or four ylidic systems in their molecular structure are described as stable compounds. Synthesis of some bridged 1,1’-disubstituted 4,4’-bipyridinium dimethylides in which 1,4- or 1,3-phenylene spacers may be used, provide some new macromolecular cycloimmonium ylides with spatially extended π-bonding system. These compounds were obtained by the chemical conversion of 4,4’-bipyridinium salts as viologens or bis-viologens, with acylating or carbamoylating agents, in basic media. The characterisation of all compounds has been mainly performed by 1H and 13C NMR spectroscopy.