Beiträge zur ökologischen chemie—LXI : Photoreaktionen des aldrin/dieldrin-metaboliten dihydrochlordendicarbonsäure (4,5,6,7,8,8-hexachloro-4,7-methano-3a,4,7,7a-tetrahydroindan-1,3-dicarbonsäure)

Abstract

Dicarboxylic acid ( 1) and its dimethylester ( 2) respectively were irradiated in solutions and in gaseous phase by UV-light of a high pressure mercury lamp with emission above 230 nm. Immersion wells of pyrex and quartz were used for the irradiation experiments. After an irradiation with UV-light having long wavelengths (λ > 300 nm), followed by a diazomethane treatment of the reaction mixture, compounds 5–11 could be isolated from solutions of the dicarboxylic acid ( 1) in acetone. Dimethylester ( 2) revealed comparable results. Compounds 3 and 4 were obtained by irradiating the dimethylester ( 2) in n-hexane and water/methanol respectively with wave-lengths below 300 nm. The dimethylester ( 2) gaseously distributed in air, yielded two isomeric products and a dechlorination product by irradiation with UV-light (λ < 300 nm). The bridged compound 5 is one of the isomeric photoproducts. This contribution mainly consists in the structural elucidation of products being formed under the influence of UV-light. The spectroscopical data of compounds 1–11 resulting in the proposed structures given in Fig 1 are discussed in the following text.