Partial but regio- and stereoselective dechlorination takes place if polychlorinated oligocyclic insecticides (Diels-Alder adducts and dimers of hexachlorocyclopentadiene) are electrolysed in methanol solution at lead cathodes. The products are detected and identified by GC/MS, IR and NMR spectroscopy. The structure of the product 2 formed from Mirex® is confirmed by an X-ray structural analysis.

The preparative electroreduction of the three methyl monochlorobenzoates, the six methyl dichlorobenzoates, and methyl 2,3,4-trichlorobenzoate in different solvent-supporting electrolytes (SSE) was studied. The rate of the dechlorination, which is the main reaction, is dependent on the substitution pattern. Pronounced regioselectivity is therefore observed in case of the oligochloro derivatives. Hydrogenation of the benzene ring and reduction of the methoxycarbonyl group with formation of a hydroxymethyl group are observed as side-reactions. Quantum chemical calculations on the reaction mechanism were performed. The theoretical results are in accordance with the experimental observations.

Chlorinated Insecticides, Electrochemical Reduction, Endosulfane, Dechlorination, X-Ray (R ) Partial dechlorination takes place if Endosulfane is electrolysed in methanol solution at lead cathodes. The products are detected and identified by GC/MS, IR and NMR spectroscopy. The structure of the product 2 is confirmed by an X-ray structural analysis.

Radical anions of alkyl a-oxocarbothioates and a-oxocarbodithioates are generated by in siru electroreduction. Their spin density distribution and configuration are discussed in terms of the ESR spectra and semiempirical (McLachlan-type and AMl) MO calculations.

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