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Cochrane, W.P.* ; Parlar, H.A. ; Gäb, S. ; Korte, F.

Structural elucidation of the chlordene isomer constituents of technical chlordane.

J. Agric. Food Chem. 23, 882-886 (1975)

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Open Access Green möglich sobald Postprint bei der ZB eingereicht worden ist.

Abstract
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The technical chlordane constituents designated α-, β-, and γ-chlordene are isomers of chlordene (C10H6Cl6). These isomers are formed via the rearrangement of chlordene by the action of Cl2 or free-radical initiating agents, and they no longer possess the cyclodiene-type structure. Elucidation of these isomeric structures involved various chemical derivitization reactions. Oxidation with chromic oxide yielded ketones and epoxides while reduction with Zn-HOAc or CrCl2 produced mono- and didechlorinated homologs. Photoisom-ers, in which the two original ClC=CCl bonds had been cross-linked, resulted from their unsensitized uv irradiation. Spectral confirmation of structure was obtained by 1H NMR and gas chromatography-mass spectrometry (GC-MS) studies. It is postulated that α-chlordene is 1,2,3,5,7,8-hexa-chloro-1,3a,4,5,6,6a - hexahydro-1,4-ethenopentalene (III) and β-chlordene is 2,3,3a,4,5,7-hexa-chloro-3a,6,7,7a-tetrahydro-1,6-methano-1H-indene (XIII), with γ-chlordene (XI) being the 2,3,3a,4,5,8-hexachloro isomer of β-chlordene.

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