There has been considerable interest in the synthesis of derivatives of 7,7,8,8-tetracyano-p-quinodimethane (TCNQ) that have potential as electron acceptors in the formation of charge-transfer complexes and radical ion salts. Interest in these materials arises from their electrically conducting properties and the fact that at low temperatures many such salts exhibit superconductivity. New electron acceptors are sought in an attempt to raise the temperature at which onset of superconductivity is observed. Our approach has been to investigate the synthesis of heterocyclic analogues of TCNQ, in which isoelectromc replacement of a double bond jt-electron pair has been achieved by a heteroatom carrying a lone pair of electrons capable of 71-type conjugation. Condensation of maleic anhydride with malonomtrile, followed by treatment of the resultant salt with thionyl chloride yielded a dicyanomethylene lactone whose synthesis and chemistry was investigated as a potential precursor to the desired TCNQ analogues. The lactone reacts with alcohols and amines under mild conditions to give the corresponding hydroxy esters and amides respectively Cyclisation of the hydroxy esters was attempted by converting them to amide esters at elevated temperatures. However, thermal decomposition of the amide esters resulted and product isolation was impossible. New heterocyclic TCNQ systems based on pyrazine were also synthesised For example, 5,6-diphenyl-2,3-dicyanopyrazine was reacted with ammonia gas and condensation of the resultant dnmino derivative with malonomtrile gave the bis(dicyanomethylene) ammonium salt. This ammonium salt was used as a precursor for a range of derivatives Acidification gave the protonated (N-H) compound and reaction with tetraalkylammonium halides gave the corresponding bis(dicyanomethylene) tetraalkylammonium salts Pyrolysis of these tetraalkylammonium salts, with the elimination of the appropriate trialkylamine, resulted in the preparation of N-alkyl derivatives in reasonable yields. The charge-transfer complexing ability of these electron acceptors (N-H compound and N-alkyl derivatives) with appropriate electron donors [tetrathiafulvalene (TTF) and N,N,N’,A/'-tetramethyl-p-phenylenediamine (TMPD)] was investigated Cyclic voltammetry measurements of the N-H and N-alkyl derivatives showed that they are electrochemically reversible exhibiting one and two electron reductions respectively.