Photolysis of the toxaphene component 2,2,3-exo,5,5,8,9,9,10,10-decachlorobornane

Four major photoproducts of the toxaphene component 2,2,3-exo,5,5,8,9,9,10,10-decachlorobornane irradiated in n-hexane at 254 nm have been isolated and their structure has been characterized. The main photolytic reactions were vicinal dichloro elimination, reductive dechlorination, and isomerization. Three products still have a bornane skeleton with seven or eight chlorines, respectively. As a fourth, a heptachlorotricyclene has been formed via a photoisomerization reaction. The structural elucidation of the isolated compounds has been carried out by spectroscopic methods. Furthermore, a possible transformation pathway is discussed.