Abstract
AbstractThe insecticide endosulfan (5a,9a‐ 14C 6,7,8,9,10,10‐hexachloro‐1,5,5a,6,9,9a hexahydro‐6,9‐methano‐2,4,3‐benzodioxathiepin‐3‐oxide) was prepared from 2,3 14C‐maleic anhydride. The Diels‐Alder reaction of maleic anhydride with hexachloro‐cyclopentadiene yielded 1,4,5,6,7,7‐hexachlorobi‐cyclo [2.2.1] hept‐5‐ene‐2,3‐dicarboxylic acid anhydride. This anhydride was reduced to the corresponding carboxylic acid γ lactone with sodium boro‐hydride which was further reduced to the diol (1,4,5,6,7,7‐hexachloro‐2,3‐bis‐(hydroxymethyl) bicyclo [2. 2. 1] hept‐5‐ene) with lithium aluminum hydride. The later compound was reacted with thionyl chloride in carbon tetrachloride to give endosulfan.
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