Isolation and identification of a thermo-unstable octachlorodihydrocamphene from technical toxaphene

A new dihydrocamphene congener, 2,2,3-exo,6,8,9,10, 10- octachlorodihydrocamphene, has been isolated from the technical toxaphene using column chromatography followed by HPLC. This can be considered to be the secondly identified dihydrocamphene in the complex technical mixture. The isolated compound was unstable at temperatures up to 180°C, also under HRGC conditions of up to 200°C, and converted spontaneously to 2,2,3-exo,8,9,10α- hexachlorocamphene under elimination of Cl₂. The structure of both congeners were confirmed by MS, FTIR, ¹H- and ¹³C-NMR spectroscopy. The postulated reaction way pointed out that parts of chlorocamphenes detected in a technical mixture by GC were probably artifacts.