A STUDY OF CHEMICAL REACTIONS OF SELECTED TOXAPHENE COMPONENTS WITH SOME UNEXPECTED PRODUCTS AS A RESULT

摘要

Hydrogenation of 2,2,5-endo,6-exo,8,9,10-heptachloro-bornane (P32) in ethyl acetate using palladium on activated carbon produced 2-exo,3-endo,8,9,10-pentachloro-bornane in high yield, while from 2,2,3-exo,5-endo,6-exo, 8,9,9,10,10-decachlorobornane and 2,2,3-exo,5.5,8,9,9,10, 10-decachlorobornane, during the first step, the unexpected intermediates 2,5-endo,6-exo-8,8,9,10, 10-octachlorobor-nene-2 and 2,5,5,8,8,9,10,10-octachlorobornene-2 were formed. Heating of P32 on activated carbon formed 2,5-endo,6-exo,8,9,10-hexachlorobornene-2 as intermediate, which was quantitatively converted to 2-exo,3-endo,8,9,10-pentachlorobornane by catalytic hydrogenation. Treatment of P32 with zinc powder in diethyl ether led to 2,5-endo,8,9,10-pentachlorotricyclene instead of anticipated 2,2,8,9,10-pentachlorobornene-2. 2-exo,3-endo,6-exo,8,9,10-hexachlorobornane (Hx-Sed) and 2-exo,3-endo,6-endo,8,9, 10-hexachlorobornane (e-Hx-Sed) were isomerised into each other by heating on acidic aluminium oxide.