Beiträge zur ökologischen chemie—XLVIII: Reaktionen von dieldrin mit stickstoffdioxyd und ozon in ultraviolettem licht

Abstract

The compounds III-VII were isolated from solutions of dieldrin (I) and nitrogen tetroxide in fluorocarbon after irradiation with UV-light having long wavelengths (λ s $ ̆ 300 nm). Irradiation of solutions of dieldrin and nitrogen tetroxide in carbon tetrachloride under similar conditions yielded compounds II-VI. Compound IV was detected after irradiation of a solution of dieldrin and ozone in fluorocarbon. In the presence of nitrogen dioxide dieldrin distributed in nitrogen in gaseous state was converted mainly into photodieldrin (IX) by UV-light. Irradiation of dieldrin gaseously distributed in ozonized air yielded, as in ozonic solution, several products of higher molecular weight, which, however, were not isolated. Compound VIII, excreted in the urine of rats to which dieldrin was administered, 2 was obtained by dehydrochlorination of compound VI. Thus the structure of the metabolite 3 could be confirmed by means of a NMR- and UV-spectrum of compound VI. The spectra of compounds II-VII are discussed, from which the proposed structures given in Fig 1 are derived. Radical mechanisms are proposed for these reactions.