The synthesis and characterization of several formazans containing strong electron-withdrawing substituents (cyano and nitro) in the 3 position of the ligand backbone are described. Reactions of aryldiazonium cations with the conjugated bases of either cyanoacetic acid or nitromethane lead to 1,5-diaryl-3-cyano- or 3-nitroformazans, respectively. When these reactions are carried out in aqueous conditions, the range of aromatic groups is limited by the stability of the diazonium salt. However, 3-nitroformazans containing bulky substituents on the nitrogen atoms (2,6-dimethylphenyl, 2,4,6-trimetyhlphenyl, 2,6-diisopropylphenyl, and 3,5-ditert-butylphenyl) could be made by performing the reactions under nonaqueous and anhydrous conditions. NMR and electronic spectroscopic studies indicate that the 3-nitroformazans exist exclusively as closed ( trans-syn, s-cis) isomers whereas the 3-cyanoformazans exist as mixtures of isomers which are substrate-dependent. The crystal structures of five of the formazans are presented: two 3-nitroformazans, both of which are closed, and three 3-cyanoformazans, two of which are closed and one of which adopts an open ( trans-syn, s-trans) structure. Solid state (diffuse reflectance) spectroscopy has been employed to ascertain the isomeric preferences of the other formazans which could not be crystallographically characterized.

Forensic analysis of carbofuran residues in weathered tissue samples for evidence of Furadan exposure in vultures (Gps africanus) by HPLC gave concentration (mg/Kg dry tissue weight) ranges of bdl - 0.07 (carbofuran), bdl - 0.499 (3-ketocarbofuran) and 0.013-0.147 (3-hydroxycarbofuran) in beaks, bdl-0.65 (carbofuran), 0.024-0.190 (3-ketocarbofuran) and 0.017-0.098 (3-hydroxycarbofuran) in feet, 0.179-0.219 (3-ketocarbofuran) and 0.081-0.093 (3-hydroxycarbofuran) in crop content, 0.078-0.082 (3-ketocarbofuran) and 0.091-0.101 (3-hydroxycarbofuran) in muscle of a laced carcass and 0.006-0.014 (carbofuran), 0.590-1.010 (3-ketocarbofuran) and 0.095-0.135 (3-hydroxycarbofuran) in soil sampled from a poisoning site. These compounds were confirmed by GC-MS. The results showed that HPLC combined with GC-MS is suitable for forensic analysis of carbofuran residues in bird tissue samples and that forensic investigation should include its two toxic metabolites, 3-hydroxycarbofuran and 3-ketocarbofuran.

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The radical polymerization of styrene and n-butyl acrylate is demonstrated to proceed under controlled conditions between 125 and 130 °C in the presence of either a 1,5-dimethyl-3-phenyl-6-oxoverdazyl radical or a 1,5-dimethyl-3-ethyl-6-oxoverdazyl radical producing polymers with polydispersity indices in the 1.2−1.3 range. While polymerizations initiated with benzoyl peroxide or 1,1-azobis(cyanocyclohexane) in the presence of verdazyl radical were unsuccessful, polymerizations initiated with a styrene/verdazyl unimolecular initiator proceeded in a living fashion, although quite slowly. An increase in polymerization rate was obtained with a 1,5-dimethyl-6-oxoverdazyl radical, producing higher yields of well-defined polymers. The livingness of the resulting styrene and n-butyl acrylate homopolymers is illustrated with chain extension reactions to make well-defined diblock copolymers. These results open a new front in the development of living-radical polymerization processes, and the ability to manipulate the verdazyl structure offers the opportunity to further control and modify this process.