’H Nmr Spectra and Structure of a Unique Tetrachloropentacyclododecanone Derived from Monodechloroaldrin and Monodechloroisodrin
Some time ago we found1 that the hexachlorocyclodiene pesticides aldrin (1) isodrin (2) dieldrin (3) and endrin (4) (and several related compounds) were stereo-selectively monodehalogenated at the dichloromethylene bridge by heating with the elementary reagent Na(K)OR-DMSO (with or without added ROH) giving e.g. from aldrin and isodrin the pentachloro compounds (5), (6). The dienes (5) and (6) behave as expected when treated with acetic-sulphuric acid mixtures, dechloroaldrin giving almost entirely unrearranged acetate (7) and ca. 1% of a tetrachlorocarbonyl compound (√max 1785 vs cm.-1 m/e 310) whilst dechloroisodrin, charatteristically, gives predominantly the half-cage acetate (8).
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