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The effect of strong basic reagents on the title compounds was investigated. The dehydrochlorination of cis-chlordane proceeds rapidly to give 3-chlorochlordene, whereas its isomer, trans-chlordane, loses HCl very slowly to yield 2-chlorochlordene. The difference in rates of HCl elimination and the formation of isomeric chloro-vinyl derivatives is discussed with reference to the mechanisms of the reactions and the structures of the parent compounds. The action of basic reagents on heptachlor epoxide resulted in preferential epoxide isomerization (or rearrangement) to an allylic alcohol derivative. The structure of this α,β- unsaturated alcohol was elucidated from the characterization of the products formed by chlorination and oxidation. Ileptachlor undergoes substitution to give 1-hydroxychlordene in basic hydroxylic media. The addition reactions of tert.-butyl hypochlorite/glacial acetic acid to both heptachlor and aldrin are also mentioned.

journal - association of official analytical chemists

Cyclodiene Chemistry. II. Identification of the Derivatives Employed in the Confirmation of Heptachlor, Heptachlor Epoxide, cis-Chlordane, and frans-Chlordane Residues